Thioimideazoles useful as intermediates for preparing thiazine
US5164511A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Sep 26, 1991 |
| Grant date | Nov 17, 1992 |
| Priority date | — |
| Expiry date | Sep 26, 2011 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D233/84
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
Novel thioimidazoles are 5-carboxyaldehyde-1-methyl-4-(phenylmethyl)thioimidazole and 5-(.alpha.-aminoacetyl)-1-methyl-4-(phenylmethyl)thioimidazole acid addition salt. The latter is prepared from the former by steps comprising Grignard addition to form 5-(1-hydroxyethyl)-1-methyl-4-(phenylmethyl)thioimidazole, oxidizing the hydroxy compound to form the corresponding ketone, brominating under acidic conditions to form the bromoacetyl derivative, converting the bromo in the bromoacetyl derivative to N,N-diformylamino and then hydrolyzing. The latter thioimidazole is an intermediate for forming 5-methylimidazo[4,5-e]-1,2-thiazin-4(5H)-one, that is neamphine, and for forming 3-chloro-(5-methylimidazo) [4,5-e]-1,2-thiazin-4(5H)-one, that is 3-chloroneamphine.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.