DE2826452A1 - Verfahren zur herstellung von substituierten guanidinen - Google Patents
Verfahren zur herstellung von substituierten guanidinenInfo
- Publication number
- DE2826452A1 DE2826452A1 DE19782826452 DE2826452A DE2826452A1 DE 2826452 A1 DE2826452 A1 DE 2826452A1 DE 19782826452 DE19782826452 DE 19782826452 DE 2826452 A DE2826452 A DE 2826452A DE 2826452 A1 DE2826452 A1 DE 2826452A1
- Authority
- DE
- Germany
- Prior art keywords
- substituted
- substituents
- salt
- compound
- thiourea
- 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.)
- Granted
Links
- 150000002357 guanidines Chemical class 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 10
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
- AOPRFYAPABFRPU-UHFFFAOYSA-N amino(imino)methanesulfonic acid Chemical compound NC(=N)S(O)(=O)=O AOPRFYAPABFRPU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- OYQJFWIXVCUZEO-UHFFFAOYSA-N hydrogen peroxide;thiourea Chemical compound OO.NC(N)=S OYQJFWIXVCUZEO-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- -1 ethyl ethyl group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- GKVUQZXKYCDPBJ-UHFFFAOYSA-N N-benzyl-N'-methylmethanimidamide Chemical compound C(C1=CC=CC=C1)NC=NC GKVUQZXKYCDPBJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- ZILSBZLQGRBMOR-UHFFFAOYSA-N 1,3-benzodioxol-5-ylmethanamine Chemical compound NCC1=CC=C2OCOC2=C1 ZILSBZLQGRBMOR-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- VGECWZHYDMFANY-UHFFFAOYSA-N 1-benzyl-1-methylthiourea Chemical compound NC(=S)N(C)CC1=CC=CC=C1 VGECWZHYDMFANY-UHFFFAOYSA-N 0.000 description 1
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- ZRALSGWEFCBTJO-UHFFFAOYSA-O guanidinium Chemical compound NC(N)=[NH2+] ZRALSGWEFCBTJO-UHFFFAOYSA-O 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001734 parasympathetic effect Effects 0.000 description 1
- 210000001002 parasympathetic nervous system Anatomy 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2553377A GB1587258A (en) | 1977-06-17 | 1977-06-17 | Production of substituted guanidines |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2826452A1 true DE2826452A1 (de) | 1979-01-11 |
DE2826452C2 DE2826452C2 (de) | 1987-01-22 |
Family
ID=10229222
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19782826452 Expired DE2826452C2 (de) | 1977-06-17 | 1978-06-16 | Verfahren zur Herstellung von substituierten Guanidinen |
Country Status (8)
Country | Link |
---|---|
JP (1) | JPS5448714A (fi) |
AU (1) | AU520839B2 (fi) |
CA (1) | CA1083603A (fi) |
DE (1) | DE2826452C2 (fi) |
DK (1) | DK158977C (fi) |
GB (1) | GB1587258A (fi) |
NL (1) | NL187856C (fi) |
NZ (1) | NZ187557A (fi) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6043414U (ja) * | 1983-08-29 | 1985-03-27 | 本田技研工業株式会社 | 自動二輪車等のヒ−タ装置 |
US4781866A (en) * | 1985-03-15 | 1988-11-01 | Mcneilab, Inc. | Process for producing amidine sulfonic acid intermediates for guanidines |
US4656270A (en) * | 1985-03-15 | 1987-04-07 | Mcneilab, Inc. | Process for producing guanidines such as linogliride |
US4656291A (en) * | 1985-03-15 | 1987-04-07 | Mcneilab, Inc. | Process for producing amidine sulfonic acids |
US4693850A (en) * | 1985-03-15 | 1987-09-15 | Mcneilab, Inc. | Methane sulfonic acid derivatives |
US4851094A (en) * | 1985-03-15 | 1989-07-25 | Mcneilab, Inc. | Process for producing amidine sulfonic acid intermediates for guanidines |
US5948939A (en) * | 1986-09-10 | 1999-09-07 | Syntex (U.S.A.) Inc. | Selective amidination of diamines |
DE3774975D1 (de) * | 1986-09-10 | 1992-01-16 | Syntex Inc | Selektive amidinierung von diaminen. |
JPH0655730B2 (ja) * | 1987-07-17 | 1994-07-27 | ザ ヌトラスウィート カンパニー | 強力甘味剤 |
AU3578489A (en) * | 1988-07-12 | 1990-02-05 | Nutrasweet Company, The | High potency sweetening agents |
GB9309321D0 (en) * | 1993-05-06 | 1993-06-16 | Wellcome Found | Process for the preparation of ng-monoalkyl-l-arginine derivatives |
CN102363602A (zh) * | 2011-09-20 | 2012-02-29 | 科迈化工股份有限公司 | 以双氧水为氧化剂生产硫化促进剂dpg的方法 |
CN102363601A (zh) * | 2011-09-20 | 2012-02-29 | 科迈化工股份有限公司 | 以双氧水为氧化剂生产橡胶促进剂dgp的方法 |
CN110407720B (zh) * | 2019-08-20 | 2021-07-27 | 西安近代化学研究所 | 一种碘催化硫脲脱硫制备取代胍的合成方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB973882A (en) * | 1959-12-23 | 1964-10-28 | Wellcome Found | Benzyl-guanidines,their preparation and pharmaceutical compositions containing them |
-
1977
- 1977-06-17 GB GB2553377A patent/GB1587258A/en not_active Expired
-
1978
- 1978-06-13 NZ NZ18755778A patent/NZ187557A/xx unknown
- 1978-06-14 DK DK265978A patent/DK158977C/da active
- 1978-06-15 AU AU37154/78A patent/AU520839B2/en not_active Expired
- 1978-06-15 JP JP7157778A patent/JPS5448714A/ja active Granted
- 1978-06-16 DE DE19782826452 patent/DE2826452C2/de not_active Expired
- 1978-06-16 CA CA305,594A patent/CA1083603A/en not_active Expired
- 1978-06-16 NL NL7806526A patent/NL187856C/xx not_active IP Right Cessation
Non-Patent Citations (2)
Title |
---|
Beilstein: Handb., Bd. 3, 1. Erg., 36 * |
Liebigs Ann.Chem., 722, 1969, 98-109 * |
Also Published As
Publication number | Publication date |
---|---|
CA1083603A (en) | 1980-08-12 |
NZ187557A (en) | 1980-08-26 |
GB1587258A (en) | 1981-04-01 |
JPS5448714A (en) | 1979-04-17 |
NL187856C (nl) | 1992-02-03 |
JPS5748106B2 (fi) | 1982-10-14 |
AU520839B2 (en) | 1982-03-04 |
AU3715478A (en) | 1979-12-20 |
DK158977B (da) | 1990-08-13 |
DK158977C (da) | 1991-01-21 |
NL7806526A (nl) | 1978-12-19 |
DE2826452C2 (de) | 1987-01-22 |
DK265978A (da) | 1978-12-18 |
NL187856B (nl) | 1991-09-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
OD | Request for examination | ||
D2 | Grant after examination | ||
8364 | No opposition during term of opposition | ||
8339 | Ceased/non-payment of the annual fee |