Water → HCID 70117039, compound

HRID 868939Notes

Reaction equation

HRID 868939 reaction equation
[CH:1]([C:3]1[N:4]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1)=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][C:3]1[N:4]([S:14]([N:17]([CH3:19])[CH3:18])(=[O:15])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19825137HCID 19825137, compound

Product 1

HCID 70117039HCID 70117039, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Formyl-N,N-dimethyl-4-phenyl-1H-imidazole-1-sulfonamide (221 mg, 0.79 mmol) was dissolved in anhydrous MeOH (10 mL) and NaBH4 (89 mg, 2.37 mmol) was added in portions. Gas evolved and the suspension was stirred at room temperature. After 30 min, the crude reaction mixture was poured into H2O and extracted with EtOAc (3×20 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated to give crude 2-(hydroxymethyl)-N,N-dimethyl-4-phenyl-1H-imidazole-1-sulfonamide, which was used directly in the next reaction.

Workup

  1. customthe crude reaction mixture
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-39ae9f26a33747a4a5fa8d8abefc4b19
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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