Potassium Carbonate → N-[4-(2-Amino-4-cyanomethoxy-phenylsulfanyl)-phenyl]-acetamide

HRID 883913Notes

Reaction equation

HRID 883913 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.Br[CH2:21][C:22]#[N:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH2:21][C:22]#[N:23])[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 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 67250701N-[4-(2-Amino-4-hydroxy-phenylsulfanyl)-phenyl]-acetamide

Product 1

HCID 67249992N-[4-(2-Amino-4-cyanomethoxy-phenylsulfanyl)-phenyl]-acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from Example 38b (56 mg, 0.17 mmol), 2-Bromoacetonitrile (20 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 (53 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-6c854fd593c640f2ba0654ae27b33a59
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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