Benzyl Bromide → N-[4-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenyl]-acetamide

HRID 2198003Notes

Reaction equation

HRID 2198003 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 67250701N-[4-(2-Amino-4-hydroxy-phenylsulfanyl)-phenyl]-acetamide

Product 1

HCID 68460688N-[4-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenyl]-acetamideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from Example 232b (56 mg, 0.17 mmol), benzyl bromide (21 mg, 0.17 mmol) and potassium carbonate (26 mg, 0.19 mmol) in DMF (1 mL) was stirred at room temperature 15 hr. The next day, the reaction mixture was poured onto ice and the solid collected by filtration providing the title compound (62 mg, 100%).

Workup

  1. additionThe next day, the reaction mixture was poured onto ice
  2. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-23375edf9dc743a1a9030c299c57d41d
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

Loading…