NO136193B - - Google Patents

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Info

Publication number: NO136193B
Authority: NO; Norway
Prior art keywords: thiazolidine; hydrolysis; nitrile; dimethyl; carboxylic acid
Prior art date: 1971-11-15

Application number

NO3846/72A

Other languages

English (en)

Norwegian (no)

Other versions

NO136193C (no

Inventor

H Offermanns

F Asinger

K-H Gluzek

Original Assignee

Degussa

Priority date (The priority date 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 date listed.)

1971-11-15

Filing date

1972-10-25

Publication date

1977-04-25

1972-10-25 Application filed by Degussa filed Critical Degussa

1977-04-25 Publication of NO136193B publication Critical patent/NO136193B/no

1977-08-03 Publication of NO136193C publication Critical patent/NO136193C/no

Links

VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 34
150000002825 nitriles Chemical class 0.000 claims description 17
230000007062 hydrolysis Effects 0.000 claims description 13
238000006460 hydrolysis reaction Methods 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 claims description 7
PRSDPVKGJUBIAA-UHFFFAOYSA-N 1,3-thiazolidine-4-carbonitrile Chemical compound N#CC1CSCN1 PRSDPVKGJUBIAA-UHFFFAOYSA-N 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
229960001639 penicillamine Drugs 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
230000015556 catabolic process Effects 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
239000011541 reaction mixture Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
-1 aliphatic aldehydes Chemical class 0.000 description 5
125000005521 carbonamide group Chemical group 0.000 description 5
CJCQTPCVKRWSLM-UHFFFAOYSA-N 5,5-dimethyl-2-propan-2-yl-1,3-thiazolidine-4-carboxylic acid;hydrochloride Chemical compound Cl.CC(C)C1NC(C(O)=O)C(C)(C)S1 CJCQTPCVKRWSLM-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XRKZVUKVOZHPEQ-UHFFFAOYSA-N 5,5-dimethyl-2-propan-2-yl-1,3-thiazolidine-4-carbonitrile Chemical compound CC(C)C1NC(C#N)C(C)(C)S1 XRKZVUKVOZHPEQ-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000007306 turnover Effects 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
HHQSUSGDCHSDTO-UHFFFAOYSA-N 5,5-dimethyl-2-propan-2-yl-4h-1,3-thiazole Chemical compound CC(C)C1=NCC(C)(C)S1 HHQSUSGDCHSDTO-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229950005499 carbon tetrachloride Drugs 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
150000003549 thiazolines Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000013638 trimer Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Thiazole And Isothizaole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO3846/72A 1971-11-15 1972-10-25 Fremgangsm}te til fremstilling av penicillamin. NO136193C (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2156601A DE2156601C3 (de)	1971-11-15	1971-11-15	Verfahren zur Herstellung von DX-PeniciUamin

Publications (2)

Publication Number	Publication Date
NO136193B true NO136193B (ro)	1977-04-25
NO136193C NO136193C (no)	1977-08-03

Family

ID=5825136

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3846/72A NO136193C (no)	1971-11-15	1972-10-25	Fremgangsm}te til fremstilling av penicillamin.

Country Status (21)

Country	Link
JP (1)	JPS566992B2 (ro)
AU (1)	AU472713B2 (ro)
BE (1)	BE791411R (ro)
CH (1)	CH587240A5 (ro)
CS (1)	CS191252B4 (ro)
DD (1)	DD101391A6 (ro)
DE (1)	DE2156601C3 (ro)
DK (1)	DK145624C (ro)
EG (1)	EG10782A (ro)
ES (1)	ES407956A2 (ro)
FI (1)	FI59398C (ro)
FR (1)	FR2160483B2 (ro)
GB (1)	GB1394845A (ro)
IE (1)	IE36829B1 (ro)
IL (1)	IL40829A (ro)
IT (1)	IT1045669B (ro)
NL (1)	NL175913C (ro)
NO (1)	NO136193C (ro)
SE (1)	SE405354B (ro)
YU (1)	YU39600B (ro)
ZA (1)	ZA727545B (ro)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1143608B (it) *	1976-10-09	1986-10-22	Degussa	Procedimento per la produzione di tiazolidin-4-carbonitrili e loro conversione in d,l-cisteina
DE2716476C2 (de) *	1977-04-14	1985-07-11	Robert Bosch Gmbh, 7000 Stuttgart	Niveauregeleinrichtung für Kraftfahrzeuge
JPS57195391U (ro) *	1981-06-05	1982-12-10

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH540234A (de) *	1968-09-06	1973-08-15	Degussa	Verfahren zur Herstellung von Penicillamin
JPS584587B2 (ja) *	1977-06-14	1983-01-27	松下電器産業株式会社	回転式粘性剤塗布方法およびその装置

0
- BE BE791411D patent/BE791411R/xx active
1971
- 1971-11-15 DE DE2156601A patent/DE2156601C3/de not_active Expired
- 1971-12-30 SE SE7116964A patent/SE405354B/xx unknown
1972
- 1972-10-10 NL NLAANVRAGE7213689,A patent/NL175913C/xx active Search and Examination
- 1972-10-17 FI FI2867/72A patent/FI59398C/fi active
- 1972-10-18 YU YU2599/72A patent/YU39600B/xx unknown
- 1972-10-24 ZA ZA727545A patent/ZA727545B/xx unknown
- 1972-10-25 NO NO3846/72A patent/NO136193C/no unknown
- 1972-10-25 ES ES407956A patent/ES407956A2/es not_active Expired
- 1972-11-01 GB GB5037572A patent/GB1394845A/en not_active Expired
- 1972-11-10 DK DK559972A patent/DK145624C/da not_active IP Right Cessation
- 1972-11-10 IE IE1537/72A patent/IE36829B1/xx unknown
- 1972-11-11 EG EG458/72A patent/EG10782A/xx active
- 1972-11-13 DD DD166822A patent/DD101391A6/xx unknown
- 1972-11-13 AU AU48812/72A patent/AU472713B2/en not_active Expired
- 1972-11-13 CH CH1648372A patent/CH587240A5/xx not_active IP Right Cessation
- 1972-11-13 IT IT53994/72A patent/IT1045669B/it active
- 1972-11-14 JP JP11419972A patent/JPS566992B2/ja not_active Expired
- 1972-11-14 CS CS727709A patent/CS191252B4/cs unknown
- 1972-11-14 IL IL40829A patent/IL40829A/xx unknown
- 1972-11-15 FR FR7240521A patent/FR2160483B2/fr not_active Expired

Also Published As

Publication number	Publication date
IL40829A (en)	1975-06-25
NL175913C (nl)	1985-01-16
FR2160483B2 (ro)	1974-08-19
IL40829A0 (en)	1973-01-30
FR2160483A2 (ro)	1973-06-29
AU4881272A (en)	1974-05-16
AU472713B2 (en)	1976-06-03
DE2156601A1 (de)	1973-05-24
YU259972A (en)	1982-06-30
SE405354B (sv)	1978-12-04
NL7213689A (ro)	1973-05-17
CH587240A5 (ro)	1977-04-29
IT1045669B (it)	1980-06-10
JPS4861421A (ro)	1973-08-28
ZA727545B (en)	1973-07-25
FI59398B (fi)	1981-04-30
DE2156601B2 (de)	1978-10-19
IE36829B1 (en)	1977-03-02
DD101391A6 (ro)	1973-11-12
BE791411R (fr)	1973-03-01
IE36829L (en)	1973-05-15
GB1394845A (en)	1975-05-21
ES407956A2 (es)	1975-11-01
DK145624C (da)	1983-07-11
FI59398C (fi)	1981-08-10
DE2156601C3 (de)	1979-06-07
JPS566992B2 (ro)	1981-02-14
EG10782A (en)	1976-12-31
NO136193C (no)	1977-08-03
CS191252B4 (en)	1979-06-29
YU39600B (en)	1985-03-20
DK145624B (da)	1983-01-03

Publication	Publication Date	Title
Davidson et al.	1956	The pyrolysis of amides
GB1463266A (en)	1977-02-02	Preparation of hydroxypivaldehyde
US2462433A (en)	1949-02-22	Preparation of organic thiocyanates and isothiocyanates
DK147972B (da)	1985-01-21	Fremgangsmaade til fremstilling af en alfa-aminosyreamidoploesning
NO136193B (ro)	1977-04-25
US2509859A (en)	1950-05-30	Nitriles from butadiene and hydrogen cyanide
US2844589A (en)	1958-07-22	Process for the preparation of belta2-oxazoline
JP4049534B2 (ja)	2008-02-20	Ｏ−アルキル−ｎ−シアノアセトイミデ−トの製造方法
US2431468A (en)	1947-11-25	Method of preparing unsaturated amides
DK158837B (da)	1990-07-23	Fremgangsmaade til fremstilling af p-hydroxyphenylglycin.
US2064564A (en)	1936-12-15	Preparation of monomethylol ketones
US4045479A (en)	1977-08-30	Process of preparing penicillamine
US3946069A (en)	1976-03-23	Process of making penicillamine
US2576306A (en)	1951-11-27	Substituted imidazolidine compounds and method for preparing them
SU445662A1 (ru)	1974-10-05	Способ получени 4-амино-3,5,6трихлорпиколиновой кислоты
US2330223A (en)	1943-09-28	Aminothiazole from chloroacetal
JPS6136270A (ja)	1986-02-20	２‐アルキル‐４，５‐ジヒドロキシメチルイミダゾールの製法
US4061674A (en)	1977-12-06	Process of making penicillamine
US2792395A (en)	1957-05-14	Preparation of guanamines
US3406191A (en)	1968-10-15	Method of producing methyl isothiocyanate
US3975402A (en)	1976-08-17	Preparation of N-˜(1-ethyl-pyrrolidinyl-2)-methyl]-2-methoxy-5-sulphamoyl-benzamide
GB728522A (en)	1955-04-20	Improvements in the production of pure adiponitrile
US4614803A (en)	1986-09-30	Process for the preparation of dry alkali metal salts of 1,8-naphthalimide
SU451695A1 (ru)	1974-11-30	Способ получени -метил-меркаптопропионового альдегида
SU548600A1 (ru)	1977-02-28	Способ получени 3,4-ксилидина