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

HRID 35495Notes

Reaction equation

HRID 35495 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[CH:8]=[C:9]([S:21](Cl)(=[O:23])=[O:22])[CH:10]=[CH:11][C:12]=1[NH:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15]>O1CCCC1>[C:1]([NH:5][S:21]([C:9]1[CH:10]=[CH:11][C:12]([NH:13][S:14]([C:17]([F:20])([F:18])[F:19])(=[O:16])=[O:15])=[C:7]([Cl:6])[CH:8]=1)(=[O:23])=[O:22])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 135378843-Chloro-4-(trifluoromethanesulfonamido)benzenesulfonyl chloride

Product 1

HCID 13422952N-t-butyl-3-chloro-4-(trifluoromethanesulfonamido)benzenesulfonamideYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of t-butylamine (0.6 g) and 3-chloro-4-(trifluoromethanesulfonamido)benzenesulfonyl chloride (1.5 g) in tetrahydrofuran (20 ml) was allowed to stand overnight. The resultant mixture was concentrated and shaken with chloroform and 5% aqueous hydrochloric acid. The chloroform extract was concentrated and recrystallized from toluene to give 1.03 g of N-t-butyl-3-chloro-4-(trifluoromethanesulfonamido)benzenesulfonamide (Compound No. 18). M.P., 123°-127.5° C.

Workup

  1. concentrationThe resultant mixture was concentrated
  2. extractionThe chloroform extract
  3. concentrationwas concentrated
  4. customrecrystallized from toluene

Sources & evidence

ORD record
ord-5aeab631a5bd4a849cb17aedb1611dd1
Source dataset
uspto-grants-1988_08
Patent number
US04767446

Reaction notes

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