Benzyl Bromide → 4-Amino-3-(benzylthio)benzonitrile

HRID 520935Notes

Reaction equation

HRID 520935 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[SH:10].Br[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[S:10][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 155439364-Amino-3-sulfanylbenzonitrile

Product 1

HCID 866909904-Amino-3-(benzylthio)benzonitrileYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following General Procedure A, the title compound (615 mg, 79%) was prepared from 4-amino-3-mercaptobenzonitrile (486 mg, 3.24 mmol), (bromomethyl)benzene (0.38 ml, 3.24 mmol) and K2CO3 (2.2 g, 16.20 mmol) in DMF (10 ml).

Sources & evidence

ORD record
ord-67a458b697184d88a553dbe54147052f
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

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