Methane → N′-(4-Acetylphenyl)-N,N-dimethylsulfamide

HRID 442254Notes

Reaction equation

HRID 442254 reaction equation
[CH3:1][N:2]([CH3:7])[S:3](Cl)(=[O:5])=[O:4].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1.C>N1C=CC=CC=1>[C:15]([C:12]1[CH:13]=[CH:14][C:9]([NH:8][S:3]([N:2]([CH3:7])[CH3:1])(=[O:5])=[O:4])=[CH:10][CH:11]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 297MethaneHCID 7468p-AminoacetophenoneHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 4474532N′-(4-Acetylphenyl)-N,N-dimethylsulfamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dimethylsulfamoyl chloride (14.4 g., 0.10 mole) is added dropwise to p-aminoacetophenone (13.5 g., 0.10 mole) in pyridine (60 ml.) at 10°-15° C. The mixture is stirred at room temperature overnight and then added to excess 6N HC1 to give 14.1 g. (58%) of solid. The solid is dissolved in base, treated with charcoal, reprecipitated with dil. HC1, and recrystallized from water-isopropanol to give 8.9 g. (37%) of the above pure intermediate, m.p. 129°-130° C.

Workup

  1. additionadded to excess 6N
  2. customto give 14.1 g
  3. dissolutionThe solid is dissolved in base
  4. customreprecipitated with dil. HC1
  5. customrecrystallized from water-isopropanol
  6. customto give 8.9 g

Sources & evidence

ORD record
ord-bfd725e216c6443d80b14d52354a5324
Source dataset
uspto-grants-1977_08
Patent number
US04044151

Reaction notes

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