Sodium borohydride → ethyl 2-[2-(4-cyanophenyl)-2-hydroxy-1-ethylthio]-3H-imidazole-4-carboxylate

HRID 844271Notes

Reaction equation

HRID 844271 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:22])[CH2:10][S:11][C:12]2[NH:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][N:13]=2)=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CO>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([OH:22])[CH2:10][S:11][C:12]2[NH:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][N:13]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22612522ethyl 2-[2-(4-cyanophenyl)-2-oxo-ethylthio]-3H-imidazole-4-carboxylate

Product 1

HCID 22612527ethyl 2-[2-(4-cyanophenyl)-2-hydroxy-1-ethylthio]-3H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Step A (6.91 g, 21.9 mmol) was suspended in methanol (50 mL). Sodium borohydride (829 mg, 21.9 mmol) was added in portions at 0° C., and the suspension was stirred until it became homogeneous (1 hour). The reaction was quenched by the addition of saturated aqueous ammonium chloride until hydrogen evolution ceased. The resulting precipitate was filtered and washed with water (2×25 mL) to provide the title product as a white solid which was sufficiently pure for use in the next step.

Workup

  1. custom(1 hour)
  2. customThe reaction was quenched by the addition of saturated aqueous ammonium chloride until hydrogen evolution
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water (2×25 mL)

Sources & evidence

ORD record
ord-50d741ec296b45cfbcc61b2f50b60235
Source dataset
uspto-grants-2002_04
Patent number
US06380228B1

Reaction notes

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