p-Toluenesulfonic acid → N-Benzyl-2-phenylacetamide

HRID 1265956Notes

Reaction equation

HRID 1265956 reaction equation
C[Si](C)(C)[C:3]1[CH:4]=[C:5]([CH2:9][C:10]([OH:23])(P(=O)(OC)OC)P(=O)(OC)OC)[CH:6]=[CH:7][CH:8]=1.[CH2:26]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[CH2:26]([NH:33][C:10](=[O:23])[CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7504Benzylamine2×HCID 11144043Tetramethyl m-trimethylsilylphenyl-1-hydroxy-ethylidenebis(phosphonate)2×

Product 1

HCID 277826N-Benzyl-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The iodo derivative 53 was hydrolysed as described under general procedures to give the title compound as an orange colored powder in quantitative yield. Reaction of dimethyl phenylacetylphosphonate (50b) with benzylamine To a solution of the phosphonate 50b in CHCl3 (5 ml) was added molecular sieves (4A, 0.25 g) followed by benzylamine (0.11 g, 1 mmol). After 0.5 h a catalytic amount of TsOH was added and the mixture was stirred for 2 h. The mixture was filtered and flash chromatography (silica, 3:7 EtOAc/hexane) of the filtrate provided N-benzylphenylacetamide (61), as determined by comparison with an authentic sample.

Workup

  1. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-544493d03b6348d69e079fc39877511e
Source dataset
uspto-grants-2003_04
Patent number
US06548042B2

Reaction notes

Loading…