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

HRID 477910Notes

Reaction equation

HRID 477910 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-8a40133cf36e4f53a89e812b711a207a
Source dataset
uspto-grants-1989_12
Patent number
US04889848

Reaction notes

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