Dimethylamine methanol → N-[5-chloro-2-(dimethylsulfamoyl)benzyl]acetamide

HRID 1015749Notes

Reaction equation

HRID 1015749 reaction equation
CO.[CH3:3][NH:4][CH3:5].[C:6]([NH:9][CH2:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[S:18](Cl)(=[O:20])=[O:19])(=[O:8])[CH3:7]>CO.O1CCCC1>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]([S:18](=[O:20])(=[O:19])[N:4]([CH3:5])[CH3:3])=[C:11]([CH:16]=1)[CH2:10][NH:9][C:6](=[O:8])[CH3:7]

Participants

5

Reactant 2

HCID 22497844Dimethylamine methanolHCID 866508292-[(Acetylamino)methyl]-4-chlorobenzenesulfonyl chloride

Product 1

HCID 66877112N-[5-chloro-2-(dimethylsulfamoyl)benzyl]acetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(Step 1) To a solution of 2N dimethylamine methanol solution (7.51 ml) in methanol (15 ml) was added dropwise a suspension of 2-[(acetylamino)methyl]-4-chlorobenzenesulfonyl chloride (2.12 g) in tetrahydrofuran (5 ml) under ice-cooling. The mixture was allowed to warm to room temperature, and stirred for 3 hr. The reaction mixture was quenched with water, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give N-[5-chloro-2-(dimethylsulfamoyl)benzyl]acetamide (1.77 g) as a white solid.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-74ba9b8514fd47f9b611f683b5aeb474
Source dataset
uspto-grants-2011_07
Patent number
US07985862B2

Reaction notes

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