Tert-Butylamine → N-t-butyl-3-methyl-4-(trifluoromethanesulfonamido)benzenesulfonamide

HRID 35500Notes

Reaction equation

HRID 35500 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([S:16](Cl)(=[O:18])=[O:17])[CH:5]=[CH:6][C:7]=1[NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10].[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21]>O1CCCC1>[C:20]([NH:24][S:16]([C:4]1[CH:5]=[CH:6][C:7]([NH:8][S:9]([C:12]([F:15])([F:14])[F:13])(=[O:11])=[O:10])=[C:2]([CH3:1])[CH:3]=1)(=[O:18])=[O:17])([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 13194853HCID 13194853, compound

Product 1

HCID 13194854N-t-butyl-3-methyl-4-(trifluoromethanesulfonamido)benzenesulfonamideYield 34.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Methyl-4-(trifluoromethanesulfonamido)benzenesulfonyl chloride (1.5 g) was added to tetrahydrofuran (40 ml) containing t-butylamine (0.65 g), and the resultant mixture was allowed to stand at room temperature overnight. The reaction mixture was concentrated and extracted with chloroform. The extract was washed with 5% hydrochloric acid and water in order, dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from benzene and then from toluene to give 0.57 g of N-t-butyl-3-methyl-4-(trifluoromethanesulfonamido)benzenesulfonamide (Compound No. 16). M.P., 139.5°-140.5° 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. customThe residue was recrystallized from benzene

Sources & evidence

ORD record
ord-efe5e0d0c4ae41938cfc06ca65b41b15
Source dataset
uspto-grants-1988_08
Patent number
US04767446

Reaction notes

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