N-methyl-2-pyrrolidone → 3-Aminomethyl-N-tert-butyl-5-trifluoromethyl-benzenesulfonamide

HRID 42343Notes

Reaction equation

HRID 42343 reaction equation
NCC1C=CC(S([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=O)=O)=CC=1C.Br[C:19]1[CH:20]=[C:21]([S:29](Cl)(=[O:31])=[O:30])[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1.[CH3:33][N:34]1C(=O)CCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[NH2:34][CH2:33][C:19]1[CH:20]=[C:21]([S:29]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])(=[O:31])=[O:30])[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 27786103-Bromo-5-(trifluoromethyl)benzenesulfonyl chlorideHCID 582753444-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide

Product 1

HCID 671611623-Aminomethyl-N-tert-butyl-5-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
150 °C

Procedure

3-Aminomethyl-N-tert-butyl-5-trifluoromethyl-benzenesulfonamide was synthesized in a manner analogous to 4-Aminomethyl-N-tert-butyl-3-methyl-benzenesulfonamide in Example 4, using 3-bromo-5-(trifluoromethyl)benzene-1-sulfonyl chloride in place of 4-bromo-3-methylbenzene-1-sulfonyl chloride. In the second step NMP was used as the solvent, Pd(dppf)Cl2 alone was used as catalyst and the reaction mixture was stirred at 150° C. for 30 min.

Sources & evidence

ORD record
ord-bc53aee8e2024ab8b13c3f5dafe5c0fa
Source dataset
uspto-grants-2013_09
Patent number
US08536187B2

Reaction notes

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