Water → HCID 22473637, compound

HRID 2183670Notes

Reaction equation

HRID 2183670 reaction equation
[BH4-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([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:10]=[CH:11][C:4]1=2.O>CO>[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[C:9]([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:10]=[CH:11][C:4]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22474161HCID 22474161, compound

Product 1

HCID 22473637HCID 22473637, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.13 g) was added in portions at 0-5° C. to a stirred suspension of 3-(benzo[b]thiophen-5-yl)-5,6-dihydroimidazo[2,1-b]thiazole-2-carboxaldehyde (0.67 g) in methanol (20 ml), then the mixture was stirred at this temperature for 45 minutes and at ambient temperature for 1.5 hours. Water (10 ml) was added dropwise, the mixture was stirred at ambient temperature for 1 hour, and the resulting solid was collected by filtration and washed with water. The solid was dissolved in ethanol, the solvent was removed in vacuo, and the residue was triturated with dichloromethane 10 ml). The resulting solid was collected by filtration and dried in vacuo to give [3-(benzo[b]thiophen-5-yl)-5,6-dihydroimidazo[2,1-b]-thiazol-2-yl]methanol (0.1 g) as a pale yellow solid, m.p. 149-150° C.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 1 hour
  2. filtrationthe resulting solid was collected by filtration
  3. washwashed with water
  4. dissolutionThe solid was dissolved in ethanol
  5. customthe solvent was removed in vacuo
  6. customthe residue was triturated with dichloromethane 10 ml)
  7. filtrationThe resulting solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-2f82ccb0b20d47a0b4cb437ceee829c7
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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