Sodium borohydride → HCID 9857138, compound

HRID 2183595Notes

Reaction equation

HRID 2183595 reaction equation
[BH4-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]2[C:8]([C:12]3[N:13]4[CH2:21][CH2:20][N:19]=[C:14]4[S:15][C:16]=3[CH:17]=[O:18])=[CH:9][CH:10]=[CH:11][C:4]1=2>CO>[S:3]1[CH:7]=[CH:6][C:5]2[C:8]([C:12]3[N:13]4[CH2:21][CH2:20][N:19]=[C:14]4[S:15][C:16]=3[CH2:17][OH:18])=[CH:9][CH:10]=[CH:11][C:4]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22473925HCID 22473925, compound

Product 1

HCID 9857138HCID 9857138, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.05 g) was added in portions over 2 minutes to a stirred suspension of 3-(benzo[b]thiophen-4-yl)-5,6-dihydroimidazo[2,1-b]thiazole-2-carboxaldehyde (0.36 g) in methanol (10 ml), then the mixture was stirred at ambient temperature for 1.5 hours. The solvent was removed in vacuo then water (20 ml) and ethyl acetate (30 ml) were added and the mixture was stirred at ambient temperature for 2 hours. The aqueous phase was separated and washed with ethyl acetate (30 ml), then the combined ethyl acetate solutions were dried (MgSO4) and the solvent was removed in vacuo at 60° C. to give [3-(benzo[b]thiophen-4-yl)-5,6-dihydroimidazo[2,1-b]thiazol-2-yl]methanol (0.315 g) as a cream solid, m.p. 145-149° C.

Workup

  1. customThe solvent was removed in vacuo
  2. additionwater (20 ml) and ethyl acetate (30 ml) were added
  3. stirringthe mixture was stirred at ambient temperature for 2 hours
  4. customThe aqueous phase was separated
  5. washwashed with ethyl acetate (30 ml)
  6. dry with materialthe combined ethyl acetate solutions were dried (MgSO4)
  7. customthe solvent was removed in vacuo at 60° C.

Sources & evidence

ORD record
ord-958abc5ee033498e93a9b4f02c99796c
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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