Triethylamine → N-methyl-2,4-dimethyl-5-(N-propionyl-N-trifluoromethanesulfonylamino)benzenesulfonamide

HRID 35503Notes

Reaction equation

HRID 35503 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[C:10]([NH:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])[C:9]([CH3:20])=[CH:8][C:7]=1[CH3:21])(=[O:5])=[O:4].C(N(CC)CC)C.[C:29](Cl)(=[O:32])[CH2:30][CH3:31]>O1CCCC1>[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[C:10]([N:12]([C:29](=[O:32])[CH2:30][CH3:31])[S:13]([C:16]([F:19])([F:17])[F:18])(=[O:14])=[O:15])[C:9]([CH3:20])=[CH:8][C:7]=1[CH3:21])(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 13300559N-methyl-2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonamide

Product 1

HCID 13537920N-methyl-2,4-dimethyl-5-(N-propionyl-N-trifluoromethanesulfonylamino)benzenesulfonamideYield 59.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-2,4-dimethyl-5-(trifluoromethanesulfonamido)benzenesulfonamide (2 g) and triethylamine (0.7 g) in tetrahydrofuran (20 ml), propionyl chloride (0.45 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. Recrystallization from a mixture of toluene and hexane gave 1.17 g of N-methyl-2,4-dimethyl-5-(N-propionyl-N-trifluoromethanesulfonylamino)benzenesulfonamide (Compound No. 81). M.P., 101°-103° C.

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
  6. customRecrystallization
  7. additionfrom a mixture of toluene and hexane

Sources & evidence

ORD record
ord-6776f03caf6e47bbb1d95b27fadaeeda
Source dataset
uspto-grants-1988_08
Patent number
US04767446

Reaction notes

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