Dimethylamine → 4-acetyl-N,N-dimethylbenzene-1-sulfonamide

HRID 1194053

Reaction equation

HRID 1194053 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:14][NH:15][CH3:16]>C1COCC1>[CH3:14][N:15]([CH3:16])[S:10]([C:7]1[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[CH:5][CH:6]=1)(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 2664184-Acetylbenzenesulfonyl chloride

Product 1

HCID 20640414-acetyl-N,N-dimethylbenzene-1-sulfonamideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Acetylbenzenesulphonyl chloride (4.0 g, 18 mmol), aqueous dimethylamine (10 ml, 55 mmol), and THF (30 ml) were stirred together for 1 h at 20° C. and then partitioned between ethyl acetate and brine. The organic layer was dried (MgSO4) and evaporated under reduced pressure and the resulting residue recrystallised from either water or ether to give p-dimethylaminosulphonylacetophenone as fine white needles (3.8 g, 93%) m.p. 98°-99° C. (H2O); δH (dmso-d6) 8.0 (4H, ABq, aryl), 2.65 (9H, S, 3×Me).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customthe resulting residue recrystallised from either water or ether

Sources & evidence

ORD record
ord-94090da0a78440cfbf0b943b1bebc324
Source dataset
uspto-grants-1989_03
Patent number
US04812470

Linked notes

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