Triethylamine → 5,6-Dihydro-3-hydroxy-2-phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide
Reaction equation
Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](Cl)=[O:4].[S:12]1[C:16]2[C:17](=[S:21])[NH:18][CH2:19][CH2:20][C:15]=2[CH:14]=[CH:13]1.C(N(CC)CC)C>C(Cl)(Cl)Cl.O>[OH-:4].[OH:4][C:3]1[N+:18]2[CH2:19][CH2:20][C:15]3[CH:14]=[CH:13][S:12][C:16]=3[C:17]=2[S:21][C:2]=1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
aa) Method A: 29.4 g of α-bromophenylacetyl chloride were added dropwise while stirring to a solution of 23.3 g of 4,5-dihydrothieno[2,3-c]pyridine-7(6H)-thione in 630 ml of chloroform, whereby care was taken that the temperature did not exceed 25°. After 30 minutes, the mixture was treated with 25.45 g of triethylamine and stirred for an additional 3 hours. The mixture was diluted with water, the organic phase was separated, washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, evaporated and the residue was chromatographed on silica gel (elution agent toluene/ethanol 95:5). There was obtained 5,6-dihydro-3-hydroxy-2 -phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide (internal salt) of m.p. 225° (dec.) (from dioxane/acetonitrile).
Workup
- customdid not exceed 25°
- customthe organic phase was separated
- washwashed with saturated aqueous sodium chloride solution
- dry with materialdried over magnesium sulfate
- customevaporated
- customthe residue was chromatographed on silica gel (elution agent toluene/ethanol 95:5)
Sources & evidence
- ORD record
- ord-a962aa76d5d0430781d03ea105af30bf
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05321021
Reaction notes
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