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

HRID 1284816Notes

Reaction equation

HRID 1284816 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. 16). 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-c0f305b611e1456eb4519bb471cb386b
Source dataset
uspto-grants-1986_01
Patent number
US04564386

Reaction notes

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