Acetyl chloride → N,N-dimethyl-3-methyl-4-(N-acetyl-N-trifluoromethanesulfonylamino)benzenesulfonamide

HRID 35501Notes

Reaction equation

HRID 35501 reaction equation
[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[C:8]([CH3:20])[CH:7]=1)(=[O:5])=[O:4].C(N(CC)CC)C.[C:29](Cl)(=[O:31])[CH3:30]>O1CCCC1>[CH3:1][N:2]([CH3:21])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:29](=[O:31])[CH3:30])[S:13]([C:16]([F:19])([F:17])[F:18])(=[O:15])=[O:14])=[C:8]([CH3:20])[CH:7]=1)(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13422930N,N-dimethyl-3-methyl-4-(trifluoromethanesulfonamido)benzenesulfonamide

Product 1

HCID 13422963N,N-dimethyl-3-methyl-4-(N-acetyl-N-trifluoromethanesulfonylamino)benzenesulfonamideYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N,N-dimethyl-3-methyl-4-(trifluoromethanesulfonamido)benzenesulfonamide (1.5 g) and triethylamine (0.65 g) in tetrahydrofuran (40 ml), acetyl chloride (0.51 g) was added, and the resultant mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated and solidified with water. The solidified product was recrystallized from a mixture of ethanol and toluene to give 1.29 g of N,N-dimethyl-3-methyl-4-(N-acetyl-N-trifluoromethanesulfonylamino)benzenesulfonamide (Compound No. 86). M.P., 148°-148.5° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customThe solidified product was recrystallized from a mixture of ethanol and toluene

Sources & evidence

ORD record
ord-bb437d8d7be3488c969f694be9edb1e1
Source dataset
uspto-grants-1988_08
Patent number
US04767446

Reaction notes

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