Acetyl chloride → N-acetyl-N-propargyl-2,4-dimethyl-5-(N-acetyl-N-trifluormethanesulfonylamino)benzenesulfonamide

HRID 35502Notes

Reaction equation

HRID 35502 reaction equation
[CH2:1]([NH:4][S:5]([C:8]1[CH:13]=[C:12]([NH:14][S:15]([C:18]([F:21])([F:20])[F:19])(=[O:17])=[O:16])[C:11]([CH3:22])=[CH:10][C:9]=1[CH3:23])(=[O:7])=[O:6])[C:2]#[CH:3].C(N(CC)CC)C.[C:31](Cl)(=[O:33])[CH3:32].[O:35]1CC[CH2:37][CH2:36]1>>[C:31]([N:4]([CH2:1][C:2]#[CH:3])[S:5]([C:8]1[CH:13]=[C:12]([N:14]([C:36](=[O:35])[CH3:37])[S:15]([C:18]([F:20])([F:21])[F:19])(=[O:16])=[O:17])[C:11]([CH3:22])=[CH:10][C:9]=1[CH3:23])(=[O:6])=[O:7])(=[O:33])[CH3:32]

Participants

5

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13300566N-propargyl-2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonamide

Product 1

HCID 13537914N-acetyl-N-propargyl-2,4-dimethyl-5-(N-acetyl-N-trifluormethanesulfonylamino)benzenesulfonamide

Procedure

To a solution of N-propargyl-2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonamide (1.5 g) and triethylamine (1.2 g) in tetrahydrofuran (20 ml), acetyl chloride (1.0 g) was added, and the resultant mixture was allowed to stand at room temperature overnight. The reaction mixture was concentrated, admixed with 5% hydrochloric acid and extracted with chloroform. The extract was concentrated to give an oily substance, which was purified by silica gel chromatography to give 1.4 g of N-acetyl-N-propargyl-2,4-dimethyl-5-(N-acetyl-N-trifluormethanesulfonylamino)benzenesulfonamide (Compound No. 75). nD20 1.5209.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with chloroform
  3. concentrationThe extract was concentrated
  4. customto give an oily substance, which
  5. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-97549260e92340c7907cf6a6c9aba82d
Source dataset
uspto-grants-1988_08
Patent number
US04767446

Reaction notes

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