Methanol → HCID 66751381, compound

HRID 2043322Notes

Reaction equation

HRID 2043322 reaction equation
[CH2:1]([NH2:3])[CH3:2].[CH3:4][N:5]([CH3:16])[S:6]([N:9]1[CH:13]=[C:12](C=O)[N:11]=[CH:10]1)(=[O:8])=[O:7].[BH4-].[Na+].O.[CH3:20]O>>[CH3:16][N:5]([CH3:4])[S:6]([N:9]1[C:13]([CH2:20][NH:3][CH2:1][CH3:2])=[CH:12][N:11]=[CH:10]1)(=[O:7])=[O:8]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 6341EthylamineHCID 4311764Sodium borohydrideHCID 103979664-Formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 66751381HCID 66751381, compoundYield 27%

Procedure

To a saturated solution of ethylamine in methanol (40 ml) was added 4-formyl-imidazole-1-sulfonic acid dimethylamide (2.5 g, 12.3 mmol) and the mixture was stirred overnight. Sodium borohydride (0.70 g, 18.5 mmol) was added and the mixture was stirred at room temperature for 3 h. Water was added and the solution was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (SiO2: dichloromethane/methanol=9:1) to yield a light yellow oil (0.785 g, 27%); MS (ISP): 233.1 ((M+H)+.).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 h
  2. extractionthe solution was extracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by flash chromatography (SiO2: dichloromethane/methanol=9:1)

Sources & evidence

ORD record
ord-3154ecadfccb4007b512f9738f24b235
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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