Methylamine → 2-benzenesulfonyl-N-methylacetamide

HRID 1977502Notes

Reaction equation

HRID 1977502 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([O:13]C)=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][NH2:16]>>[C:1]1([S:7]([CH2:10][C:11]([NH:16][CH3:15])=[O:13])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 555619Methyl phenylsulfonyl acetate

Product 1

HCID 98591842-benzenesulfonyl-N-methylacetamide

Procedure

The entire isolated, crude and moist phenylsulfonylacetic acid methyl ester (V) was transferred to a 2-L Erlenmeyer flask and dissolved in 1 L (11.7 mol) of 40% aqueous methylamine. The reaction temperature rose to 30° C. The mixture was allowed to cool to ambient temperature, and was maintained at this temperature for an additional hour, followed by cooling overnight in a refrigerator. The precipitate product (IV) was removed by filtration. The filter cake was washed with 3×300 mL of cold water. Drying the recovered white solid at 60° C. at 30 torr over potassium hydroxide flakes for 27 h yielded 402.7 g of the methylacetamide (IV), 97.3% purity by HPLC, mp 106-109° C.

Workup

  1. customrose to 30° C
  2. temperaturewas maintained at this temperature for an additional hour
  3. temperatureby cooling overnight in a refrigerator
  4. customThe precipitate product (IV) was removed by filtration
  5. washThe filter cake was washed with 3×300 mL of cold water
  6. dry with materialDrying the recovered white solid at 60° C. at 30 torr over potassium hydroxide flakes for 27 h

Sources & evidence

ORD record
ord-05e4ae14cc2043c98a12cfd08cf1263f
Source dataset
uspto-grants-2001_05
Patent number
US06232471B1

Reaction notes

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