CA1044254A - Method for the preparation of n-substituted carbamic acid salts - Google Patents
Method for the preparation of n-substituted carbamic acid saltsInfo
- Publication number
- CA1044254A CA1044254A CA241,391A CA241391A CA1044254A CA 1044254 A CA1044254 A CA 1044254A CA 241391 A CA241391 A CA 241391A CA 1044254 A CA1044254 A CA 1044254A
- Authority
- CA
- Canada
- Prior art keywords
- carbamic acid
- preparation
- reaction
- substituted carbamic
- carried out
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 title abstract description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- -1 N-SUBSTITUTED CARBAMIC ACID SALTS Chemical class 0.000 claims abstract description 4
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000007710 freezing Methods 0.000 claims description 2
- 230000008014 freezing Effects 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 abstract description 3
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
METHOD FOR THE PREPARATION OF N-SUBSTITUTED
CARBAMIC ACID SALTS . -ABSTRACT OF THE DISCLOSURE . -A method is disclosed for preparing salts of the N-substituted carbamic acid, the improvement consisting in that the amine corresponding to the nitrogenous substituent of the carbamic acid is reacted with carbon dioxide and a salt of the metal to be introduced in the carbamic acid molecule.
CARBAMIC ACID SALTS . -ABSTRACT OF THE DISCLOSURE . -A method is disclosed for preparing salts of the N-substituted carbamic acid, the improvement consisting in that the amine corresponding to the nitrogenous substituent of the carbamic acid is reacted with carbon dioxide and a salt of the metal to be introduced in the carbamic acid molecule.
Description
.:
This invent~on relat~s to the preparation of salts of :~
~ the N substituted carbamic acid having th~ follow~ng general.. formu~a : / \ .
. ~ - N - C - ~
~` R' o ~ ~e ; wherein R and R~ can be alkyl~ aryl, cycloalkyl or aralkyl ;., radicals, either saturated or unsaturated, or, as an alterna- :
. ti~e, but not æimultaneously, hydrogen, Me is a metal of the Groups IA~ , or IIB of the periodic Table~ and n is an !~ lo .inte~er sel~cted between 1 and 2~ said method heing bas~d ~;
~ on the reaction of the corre0p~nding amines with carbon ;~ dia~ide ard with salts of said metals in an alcoholic s~lvent~ -:
The reactiqn can be su~marized by the fall~wing equation : R"OH I
n ~ n C02 ~ n R- N - H~ R ~ o Me ~ HX
. wherein Mej N, R and R' have the meanings as çx~lained above, ~ i' is an alkyl radical~ X i~ an ami}le. Anions~ the me~al .j derivativ~s of w~ich are especially used, are CO= SO3~ 0 ;.~ 20 OH~ S=, SHJ Cl~ and others; for example co~pou~ds such as LiCl~
~i ~ Li2C03~ CaOJ K2~03~ KCl le~d themselves well. Among the amine~ a ~pe~ial mention is reserved by propYlamine, diethyl amin~j N,N~-~lmethyle~hyl~nediamine, whereasj among the solvents~
the us~ is ta be emphasiz~d of meth~nol and ethanal, The~reac~ion tak~s place by causing a carbon dioxide s~ream to bubble ~hrough a solution or suspension of the select-d salt ln the pre.sence of amine. A prçssure of CO~ up to 10 :
. .
:~ .
.. ~, ~. .
.:1~ - ,. :
,.', ' ' ~
kilo~rams per square centim~ter is preferred~
The temperature is maintained between th~ freezing point teimperature o~ the alcohol or the amine and th~ boiling point, and preferably between 0C aind 600C.
I~ necessary a different solvent can also be employedj~ provi-ded that it is inert towards the reaction concer~ed The reaction products of interest herein are deposlted as bulky precipitates: simultaneously~ acidic salts are formed if the anion of the ~etal salt used as the starting material is bivalent~ as can be seen in thie above r~ported pattern, whereas, for example, the amine hydrochloride is formed if chlorides are the starting salts.
The s~paration of the c~rbamates is carried out merely by filtration when the by-pro~ucts are solu~le in the r~action medium, or also by slurryin~ the reaction raw product in a solvent which selectively dissolves the carbamates. In the latter case it is poissible directly to operate in the presence of such a solvent.
:j ~i EXAMPLE
Z0 4 25 grams of LiCl are dissolved in 50 ml$ methanol in the presen~e of 12 grams of propylamine.
C0~ is caused to be absorbed by the mixture at room tempe-rature and under a partial pressure of the gas equal to the ;
atmospheric~l pressure. A white precipitate is obtained which ;~ is collected on a filter and dried. There are obtained 8.o ~l ~rams of a product which proves to be LiOCONHCH2CH2CH3.
:.~
~i~ EXAMPLE
0.05 grams of K2C03 are slurried in 50 mls of CH30H in the pr~sence of 15 grams of N~N'-dimethylethylenediamin~, 2 ~;~
is caused to be absorbed by the mixture at room temperature ~; with a partial pressurs of carbon dioxide of 1 atmosphere , :
:~ `, .
. . , ~3~5~
N~arly immediately a white product is formed~ which is coll~ct-ed on a filter ~nd dried.. Such a p~oduct, 14,8 grams~ is identi-fied as CH3 - N ~ CH2 ~ CH2 N - CH3 ;~ COOK COOK
In addition~ after a wh:ile~ a product which h~s been found to be KHC03~ precipitate~ from the moth~r liquor.
.
EXAMPLE
3~5 grams of LiCl are dissolved ~n 25 mls EtO~ in the pre~ence of 20 grams diethylamine The mi~ture i6 subjected to C02 absorption und~r not too ., ~ .
~: drastic conditions (room temperature, C02 part. pressure 1 atmosphere.~ .
:~ A white produc~ is immediately formed~ which is identifiedas Et NCOOLi ~9.2 grams). By adding ~t20 to the mother liquor ~3 Z
a produ~t is precipitated which is identified as -di~thyl- ~:
ammonium chloride (Et2NH HCi~
....
,' :"~
,, ~ .
: .,,j,:
.~
j":~
. .
, ,:,, .,j ~';,;..
: .,: ~ .
~ 4-
This invent~on relat~s to the preparation of salts of :~
~ the N substituted carbamic acid having th~ follow~ng general.. formu~a : / \ .
. ~ - N - C - ~
~` R' o ~ ~e ; wherein R and R~ can be alkyl~ aryl, cycloalkyl or aralkyl ;., radicals, either saturated or unsaturated, or, as an alterna- :
. ti~e, but not æimultaneously, hydrogen, Me is a metal of the Groups IA~ , or IIB of the periodic Table~ and n is an !~ lo .inte~er sel~cted between 1 and 2~ said method heing bas~d ~;
~ on the reaction of the corre0p~nding amines with carbon ;~ dia~ide ard with salts of said metals in an alcoholic s~lvent~ -:
The reactiqn can be su~marized by the fall~wing equation : R"OH I
n ~ n C02 ~ n R- N - H~ R ~ o Me ~ HX
. wherein Mej N, R and R' have the meanings as çx~lained above, ~ i' is an alkyl radical~ X i~ an ami}le. Anions~ the me~al .j derivativ~s of w~ich are especially used, are CO= SO3~ 0 ;.~ 20 OH~ S=, SHJ Cl~ and others; for example co~pou~ds such as LiCl~
~i ~ Li2C03~ CaOJ K2~03~ KCl le~d themselves well. Among the amine~ a ~pe~ial mention is reserved by propYlamine, diethyl amin~j N,N~-~lmethyle~hyl~nediamine, whereasj among the solvents~
the us~ is ta be emphasiz~d of meth~nol and ethanal, The~reac~ion tak~s place by causing a carbon dioxide s~ream to bubble ~hrough a solution or suspension of the select-d salt ln the pre.sence of amine. A prçssure of CO~ up to 10 :
. .
:~ .
.. ~, ~. .
.:1~ - ,. :
,.', ' ' ~
kilo~rams per square centim~ter is preferred~
The temperature is maintained between th~ freezing point teimperature o~ the alcohol or the amine and th~ boiling point, and preferably between 0C aind 600C.
I~ necessary a different solvent can also be employedj~ provi-ded that it is inert towards the reaction concer~ed The reaction products of interest herein are deposlted as bulky precipitates: simultaneously~ acidic salts are formed if the anion of the ~etal salt used as the starting material is bivalent~ as can be seen in thie above r~ported pattern, whereas, for example, the amine hydrochloride is formed if chlorides are the starting salts.
The s~paration of the c~rbamates is carried out merely by filtration when the by-pro~ucts are solu~le in the r~action medium, or also by slurryin~ the reaction raw product in a solvent which selectively dissolves the carbamates. In the latter case it is poissible directly to operate in the presence of such a solvent.
:j ~i EXAMPLE
Z0 4 25 grams of LiCl are dissolved in 50 ml$ methanol in the presen~e of 12 grams of propylamine.
C0~ is caused to be absorbed by the mixture at room tempe-rature and under a partial pressure of the gas equal to the ;
atmospheric~l pressure. A white precipitate is obtained which ;~ is collected on a filter and dried. There are obtained 8.o ~l ~rams of a product which proves to be LiOCONHCH2CH2CH3.
:.~
~i~ EXAMPLE
0.05 grams of K2C03 are slurried in 50 mls of CH30H in the pr~sence of 15 grams of N~N'-dimethylethylenediamin~, 2 ~;~
is caused to be absorbed by the mixture at room temperature ~; with a partial pressurs of carbon dioxide of 1 atmosphere , :
:~ `, .
. . , ~3~5~
N~arly immediately a white product is formed~ which is coll~ct-ed on a filter ~nd dried.. Such a p~oduct, 14,8 grams~ is identi-fied as CH3 - N ~ CH2 ~ CH2 N - CH3 ;~ COOK COOK
In addition~ after a wh:ile~ a product which h~s been found to be KHC03~ precipitate~ from the moth~r liquor.
.
EXAMPLE
3~5 grams of LiCl are dissolved ~n 25 mls EtO~ in the pre~ence of 20 grams diethylamine The mi~ture i6 subjected to C02 absorption und~r not too ., ~ .
~: drastic conditions (room temperature, C02 part. pressure 1 atmosphere.~ .
:~ A white produc~ is immediately formed~ which is identifiedas Et NCOOLi ~9.2 grams). By adding ~t20 to the mother liquor ~3 Z
a produ~t is precipitated which is identified as -di~thyl- ~:
ammonium chloride (Et2NH HCi~
....
,' :"~
,, ~ .
: .,,j,:
.~
j":~
. .
, ,:,, .,j ~';,;..
: .,: ~ .
~ 4-
Claims (4)
1. A method for the preparation of salts of N-substituted carbamic acid having the general formula:
wherein R and R' are identical or different and each represents hydrogen or an alkyl, aryl, cycloalkyl or aralkyl radical, with the proviso that R and R' cannot simultaneously represent hydrogen, Me is a metal selected from Groups IA, IIA and IIB of the Periodic Table and n is 1 or 2, which comprises reacting in a single step an amine of the formula wherein R and R' have the aforesaid meanings, with carbon dioxide and an inorganic salt of the aforesaid metal in an alcoholic solvent.
wherein R and R' are identical or different and each represents hydrogen or an alkyl, aryl, cycloalkyl or aralkyl radical, with the proviso that R and R' cannot simultaneously represent hydrogen, Me is a metal selected from Groups IA, IIA and IIB of the Periodic Table and n is 1 or 2, which comprises reacting in a single step an amine of the formula wherein R and R' have the aforesaid meanings, with carbon dioxide and an inorganic salt of the aforesaid metal in an alcoholic solvent.
2. A method according to claim 1, wherein the reaction is carried out in a low alkanol.
3. A method according to claim 1, wherein the reaction is carried out at a temperature comprised between the freezing point and the boiling point of the alcoholic solvent or the amine.
4. A method according to claim 3, wherein the reaction is carried out at a temperature between 0° and 60°C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT30340/74A IT1026906B (en) | 1974-12-10 | 1974-12-10 | PROCEDURE FOR THE PREPARATION OF SALTS OF THE SUBSTITUTED CARBAMIC ACID N |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1044254A true CA1044254A (en) | 1978-12-12 |
Family
ID=11229568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA241,391A Expired CA1044254A (en) | 1974-12-10 | 1975-12-09 | Method for the preparation of n-substituted carbamic acid salts |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS594421B2 (en) |
| AT (1) | AT359083B (en) |
| BE (1) | BE836344A (en) |
| CA (1) | CA1044254A (en) |
| CH (1) | CH624096A5 (en) |
| DE (1) | DE2555630C3 (en) |
| DK (1) | DK557175A (en) |
| ES (1) | ES443590A1 (en) |
| FR (1) | FR2294168A1 (en) |
| GB (1) | GB1494769A (en) |
| IE (1) | IE42378B1 (en) |
| IT (1) | IT1026906B (en) |
| LU (1) | LU73952A1 (en) |
| NL (1) | NL174460C (en) |
| NO (1) | NO149661C (en) |
| SE (1) | SE430602B (en) |
| SU (1) | SU906370A3 (en) |
| ZA (1) | ZA757616B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3673245D1 (en) * | 1985-05-27 | 1990-09-13 | Tosoh Corp | METHOD FOR THE PRODUCTION OF FLUORINE-CONTAINING ALIPHATIC CARBONIC ACIDS. |
| IT1277443B1 (en) * | 1995-08-04 | 1997-11-10 | Enichem Spa | PROCEDURE FOR THE PREPARATION OF SOLUTIONS OF SUBSTITUTED N-ALCYL METALLIC CARBAMATES AND THEIR USE |
| JP7072769B2 (en) | 2018-03-02 | 2022-05-23 | 国立大学法人大阪大学 | Method for Producing Group III Nitride Crystal |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3849320A (en) * | 1972-11-30 | 1974-11-19 | Mobil Oil Corp | Organic compositions containing alkali metal arylcarbamates |
-
1974
- 1974-12-10 IT IT30340/74A patent/IT1026906B/en active
-
1975
- 1975-12-04 ZA ZA757616A patent/ZA757616B/en unknown
- 1975-12-05 BE BE162500A patent/BE836344A/en not_active IP Right Cessation
- 1975-12-08 LU LU73952A patent/LU73952A1/xx unknown
- 1975-12-08 GB GB50300/75A patent/GB1494769A/en not_active Expired
- 1975-12-08 FR FR7537404A patent/FR2294168A1/en active Granted
- 1975-12-08 CH CH1594475A patent/CH624096A5/en not_active IP Right Cessation
- 1975-12-09 NL NLAANVRAGE7514363,A patent/NL174460C/en not_active IP Right Cessation
- 1975-12-09 SE SE7513878A patent/SE430602B/en unknown
- 1975-12-09 NO NO754161A patent/NO149661C/en unknown
- 1975-12-09 ES ES443590A patent/ES443590A1/en not_active Expired
- 1975-12-09 CA CA241,391A patent/CA1044254A/en not_active Expired
- 1975-12-09 AT AT933075A patent/AT359083B/en active
- 1975-12-09 DK DK557175A patent/DK557175A/en unknown
- 1975-12-10 SU SU752197059A patent/SU906370A3/en active
- 1975-12-10 DE DE2555630A patent/DE2555630C3/en not_active Expired
- 1975-12-10 IE IE2692/75A patent/IE42378B1/en unknown
- 1975-12-10 JP JP50146469A patent/JPS594421B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2555630A1 (en) | 1976-06-16 |
| JPS5182224A (en) | 1976-07-19 |
| NL174460C (en) | 1984-06-18 |
| NO149661C (en) | 1984-05-30 |
| CH624096A5 (en) | 1981-07-15 |
| ZA757616B (en) | 1976-11-24 |
| SE430602B (en) | 1983-11-28 |
| IT1026906B (en) | 1978-10-20 |
| AT359083B (en) | 1980-10-27 |
| LU73952A1 (en) | 1976-07-01 |
| BE836344A (en) | 1976-06-08 |
| SU906370A3 (en) | 1982-02-15 |
| DK557175A (en) | 1976-06-11 |
| FR2294168B1 (en) | 1979-07-20 |
| JPS594421B2 (en) | 1984-01-30 |
| NL174460B (en) | 1984-01-16 |
| ATA933075A (en) | 1980-03-15 |
| IE42378B1 (en) | 1980-07-30 |
| NL7514363A (en) | 1976-06-14 |
| NO754161L (en) | 1976-06-11 |
| ES443590A1 (en) | 1977-05-01 |
| FR2294168A1 (en) | 1976-07-09 |
| NO149661B (en) | 1984-02-20 |
| SE7513878L (en) | 1976-06-11 |
| GB1494769A (en) | 1977-12-14 |
| IE42378L (en) | 1976-06-10 |
| DE2555630B2 (en) | 1979-06-28 |
| DE2555630C3 (en) | 1980-03-13 |
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