Triethylamine → 5,6-Dihydro-3-hydroxy-2-phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide

HRID 648515Notes

Reaction equation

HRID 648515 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]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 598182Bromophenylacetyl chlorideHCID 109974524,5-dihydrothieno[2,3-c]pyridine-7(6H)-thione

Product 1

HCID 147700175,6-Dihydro-3-hydroxy-2-phenylthiazolo[3,2-a]thieno[2,3-c]pyridinium hydroxide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

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

  1. customdid not exceed 25°
  2. customthe organic phase was separated
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customthe residue was chromatographed on silica gel (elution agent toluene/ethanol 95:5)

Sources & evidence

ORD record
ord-bb692e5389b4440ba16123b9d509deab
Source dataset
uspto-grants-1988_04
Patent number
US04735940

Reaction notes

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