Dibenzylamine → N-[4-(N,N-Dibenzylglycyl)phenyl]methanesulfonamide

HRID 1613651Notes

Reaction equation

HRID 1613651 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:7][CH:6]=1)=[O:4].[CH2:16]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC(C)=O>[CH2:24]([N:23]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:2][C:3]([C:5]1[CH:15]=[CH:14][C:8]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:7][CH:6]=1)=[O:4])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7656Dibenzylamine2×HCID 15592151N-(4-(2-bromoacetyl)phenyl)methanesulfonamide

Product 1

HCID 54331090N-[4-(N,N-Dibenzylglycyl)phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4'-(2-Bromoacetyl)methanesulfonanilide (Temple, D. L. et al., J. Med. Chem., 19(5), 626-633 (1976)) (40 g) and dibenzylamine (Aldrich Chemical Co., Milwaukee, Wis. 53233) (55.2 g) were combined in acetone (550 ml) and stirred 3 hours at ambient temperature. A heavy precipitate of dibenzylamine.HBr was filtered off. The filtrate was evaporated and crystallized first from MeOH and then from 2-PrOH. This yielded the product, 4'-(2-dibenzylaminoacetyl)methanesulfonanilide (XXVI) as a crystalline solid, 42.9 g, m.p. 131°-134°, whose thin layer chromatography analysis (silica, EtOAc/hexane) and NMR indicated a single compound with the structure indicated above.

Workup

  1. filtrationHBr was filtered off
  2. customThe filtrate was evaporated
  3. customcrystallized first from MeOH

Sources & evidence

ORD record
ord-b971680e140b4c65be8b531d8c8fb5f1
Source dataset
uspto-grants-1993_03
Patent number
US05194450

Reaction notes

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