GB575145A - Improvements in or relating to the preparation of amidine salts - Google Patents
Improvements in or relating to the preparation of amidine saltsInfo
- Publication number
- GB575145A GB575145A GB334940A GB334940A GB575145A GB 575145 A GB575145 A GB 575145A GB 334940 A GB334940 A GB 334940A GB 334940 A GB334940 A GB 334940A GB 575145 A GB575145 A GB 575145A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- ether
- solution
- ammonium
- diphenoxy
- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Amidine salts are obtained by the reaction of an iminothio-ether base with a salt of ammonium or of a primary or secondary amine. In particular, from the appropriate di-iminothioether bases are obtained salts of aromatic diamidines of the general formula Am.B.X.B.Am, wherein Am represents the amidine or N-substituted amidine group, B represents an aromatic residue and X represents: (a) a direct linkage, or (b) an alkane chain (CH2)n, wherein n is an integer from 1 to 12 and in which one or more of the -CH2- groups may be replaced by an oxygen or sulphur atom or by an -NH-group, or (c) A-CR1=CR2- group, wherein R1 and R2 represent hydrogen atoms or alkyl, aralkyl or aryl groups and may be the same or different. Advantageously, the treatment is at an elevated temperature, but below that at which any substantial quantity of ammonia is evolved, and the proportions of the reactants are adjusted so that when the ammonium or amine salt is in aqueous solution and the imino thio-ether is in alcoholic solution both reactants remain in solution when such solutions are mixed at 50-80 DEG C. In examples: (1) a -e -diphenoxy pentane-4 : 41-bis-(carbonim inothiobenzyl-ether) is heated with ammonium chloride in aqueous ethyl alcohol at 60-70 DEG C. for 26 hours, the solution is decanted into acetone and the precipitated 4 : 41 - diamidino - a ,e - diphenoxy-pentane dihydrochloride is recrystallised from dilute hydrochloric acid; (2) a - - diphenoxy-propane-4 : 41-bis-(carboniminothiobenzyl-ether) in alcoholic solution is mixed with an aqueous solution of ammonium chloride and the mixture is heated at 60-70 DEG C. for 48 hours; the filtered reaction solution is poured into acetone and the a -g -diphenoxy-propane-4 : 41-bis-(carbonamidine) dihydrochloride is precipitated; (3) trans-stilbene-4 : 41-bis-(carboniminothiobenzyl-ether) in alcoholic solution is mixed with an aqueous solution of ammonium b -hydroxyethanesulphonate, the mixture is heated at 40-50 DEG C. for 30 hours and thereafter at 70 DEG C. for 4 hours to obtain trans-stilbene-4 : 41-bis-(carbonamidine)-di-b -hydroxyethanesulphonate; (4) diphenyl ether - 4 : 41 - bis - carbon - iminothiobenzyl - ether) in alcoholic solution is mixed with an aqueous solution of ammonium b -hydroxyethane sulphonate and the mixture is heated at 70 DEG C. to obtain 4 : 41-bis - (carbonamidine) - di - b - hydroxyethanesulphonate, and the solution may be treated with caustic soda to obtain the free base. Specification 549,639 also is referred to. Di-benzylthio-imino ethers used in the examples are obtained by the reaction of the corresponding nitriles with benzyl mercaptan.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB334940A GB575145A (en) | 1944-02-23 | 1944-02-23 | Improvements in or relating to the preparation of amidine salts |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB334940A GB575145A (en) | 1944-02-23 | 1944-02-23 | Improvements in or relating to the preparation of amidine salts |
Publications (1)
Publication Number | Publication Date |
---|---|
GB575145A true GB575145A (en) | 1946-02-05 |
Family
ID=9756636
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB334940A Expired GB575145A (en) | 1944-02-23 | 1944-02-23 | Improvements in or relating to the preparation of amidine salts |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB575145A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2815377A (en) * | 1953-03-30 | 1957-12-03 | Schenley Ind Inc | Di-guanyl hydrazones |
EP0315467A2 (en) * | 1987-11-06 | 1989-05-10 | LyphoMed, Inc. | Pentamidine salts useful in the treatment and prophylaxis of pneumocystis carinii pneumonia |
-
1944
- 1944-02-23 GB GB334940A patent/GB575145A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2815377A (en) * | 1953-03-30 | 1957-12-03 | Schenley Ind Inc | Di-guanyl hydrazones |
EP0315467A2 (en) * | 1987-11-06 | 1989-05-10 | LyphoMed, Inc. | Pentamidine salts useful in the treatment and prophylaxis of pneumocystis carinii pneumonia |
EP0315467A3 (en) * | 1987-11-06 | 1990-09-26 | LyphoMed, Inc. | Pentamidine salts useful in the treatment and prophylaxis of pneumocystis carinii pneumonia |
GR1000263B (en) * | 1987-11-06 | 1992-05-12 | Lyphomed Inc | Process of preparating a pentamidine salt |
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