Water → HCID 9835604, compound

HRID 2183635Notes

Reaction equation

HRID 2183635 reaction equation
[BH4-].[Na+].[S:3]1[C:7]([C:8]2[N:9]3[CH2:17][CH2:16][N:15]=[C:10]3[S:11][C:12]=2[CH:13]=[O:14])=[CH:6][C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]1=2.O>CO>[S:3]1[C:7]([C:8]2[N:9]3[CH2:17][CH2:16][N:15]=[C:10]3[S:11][C:12]=2[CH2:13][OH:14])=[CH:6][C:5]2[CH:18]=[CH:19][CH:20]=[CH:21][C:4]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22473695HCID 22473695, compound

Product 1

HCID 9835604HCID 9835604, compoundYield 37.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.144 g) was added in portions over 10 minutes to a stirred suspension of 3-(benzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]-thiazole-2-carboxaldehyde (0.73 g) in methanol (20 ml), then the mixture was stirred at ambient temperature for 2 hours and allowed to stand at ambient temperature for 18 hours. Water (35 ml) was added and the mixture was stirred at ambient temperature for 10 minutes. The resulting solid was collected by filtration and dissolved in a 9:1 mixture of dichloromethane and ethanol (50 ml). The solution was dried (Na2SO4) and the solvents were removed in vacuo to give [3-(benzo[b]thiophen-2-yl)-5,6-dihydroimidazo[2,1-b]thiazol-2-yl]methanol (0.275 g) as a brown solid, m.p. 138-140° C.

Workup

  1. waitto stand at ambient temperature for 18 hours
  2. stirringthe mixture was stirred at ambient temperature for 10 minutes
  3. filtrationThe resulting solid was collected by filtration
  4. dissolutiondissolved in a 9:1 mixture of dichloromethane and ethanol (50 ml)
  5. dry with materialThe solution was dried (Na2SO4)
  6. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-7733cb4193ef424eb88d2cc0f11bc047
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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