Dimethylamine → N,N-dimethyl-2,4-dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonamide

HRID 35499Notes

Reaction equation

HRID 35499 reaction equation
[CH3:1][C:2]1[C:7]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:6]([CH3:16])[CH:5]=[CH:4][C:3]=1[S:17](Cl)(=[O:19])=[O:18].[CH3:21][NH:22][CH3:23]>O1CCCC1>[CH3:21][N:22]([CH3:23])[S:17]([C:3]1[CH:4]=[CH:5][C:6]([CH3:16])=[C:7]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])[C:2]=1[CH3:1])(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 135378902,4-Dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonyl chloride

Product 1

HCID 13300593N,N-dimethyl-2,4-dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonamideYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,4-Dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonyl chloride (1.4 g) was added to tetrahydrofuran (20 ml) containing dimethylamine (0.6 g), and the resultant mixture was allowed to stand overnight at room temperature. The reaction mixture was concentrated, admixed with 5% hydrochloric acid and extracted with chloroform. The extract was washed with 5% hydrochloric acid and water in order, dried over anhydrous magnesium sulfate and concentrated to give an oily substance, which was purified by column chromatography with silica gel (150 ml) to give 1.0 g of N,N-dimethyl-2,4-dimethyl-3-(trifluoromethanesulfonamido)benzenesulfonamide (Compound No. 62) M.P., 70.5°-72° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with chloroform
  3. washThe extract was washed with 5% hydrochloric acid and water in order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give an oily substance, which
  7. customwas purified by column chromatography with silica gel (150 ml)

Sources & evidence

ORD record
ord-e3173e68cf8b4fb9acc3f8184e38fddf
Source dataset
uspto-grants-1988_08
Patent number
US04767446

Reaction notes

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