Potassium Carbonate → N-{4-[2-Amino-4-(3-methyl-benzyloxy)-phenylsulfanyl]-phenyl}-acetamide

HRID 883915Notes

Reaction equation

HRID 883915 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.[CH3:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24]Br.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:28]=[CH:27][CH:26]=[C:23]([CH3:24])[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 11430Potassium CarbonateHCID 12099m-Xylyl bromideHCID 67250701N-[4-(2-Amino-4-hydroxy-phenylsulfanyl)-phenyl]-acetamide

Product 1

HCID 67250731N-{4-[2-Amino-4-(3-methyl-benzyloxy)-phenylsulfanyl]-phenyl}-acetamideYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from Example 38b (28 mg, 0.085 mmol), 3-methylbenzyl bromide (13 mg, 0.096 mmol) and potassium carbonate (13 mg, 0.09 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 tile compound (32 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-10d337f52be848c8ad9a72c4ad3cf713
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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