Dimethyl Sulfate → HCID 22185718, compound

HRID 1795118Notes

Reaction equation

HRID 1795118 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)(=[O:12])=[O:11])=[O:2].[OH-].[Na+].[CH3:25]OS(OC)(=O)=O>CO.O>[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]([CH3:25])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][CH:14]=1)(=[O:12])=[O:11])=[O:2]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 22185560HCID 22185560, compound

Product 1

HCID 22185718HCID 22185718, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of N-(2-formylphenyl)-4-(trifluoromethyl)benzenesulfonamide (2.2 g, 6.6 mmol) in methanol (11 mL) is treated with a solution of sodium hydroxide (275 mg, 6.9 mmol) in water (2.4 mL). To this is added dimethylsulfate (0.64 mL, 6.8 mmol). The reaction is stirred at rt overnight, evaporated, and chromatographed on silica gel in 5% and 10% ethyl acetate-methylene chloride. The product fractions are further purified by crystallization from toluene-hexane to afford N-(2-formylphenyl)-N-methyl-4-(trifluoromethyl)benzenesulfonamide in 68% yield.

Workup

  1. customevaporated
  2. customchromatographed on silica gel in 5% and 10% ethyl acetate-methylene chloride
  3. customThe product fractions are further purified by crystallization from toluene-hexane

Sources & evidence

ORD record
ord-0f2f8ca19ba7479394e8af0bed3273fc
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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