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Benzyl Bromide → 2-(Benzylthio)-5-chloroaniline

HRID 70425
Notes
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Reaction equation

HRID 70425 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].Br[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:11]([S:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[NH2:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 120002-Amino-4-chlorobenzenethiol

Product 1

HCID 126182102-(Benzylthio)-5-chloroanilineYield 33.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following General Procedure A, the title compound (560 mg, 33%) was prepared from 2-amino-4-chlorobenzenethiol (1.08 g, 6.77 mmol), (bromomethyl)benzene (0.8 ml, 6.77 mmol) and K2CO3 (3.18 g, 23.04 mmol) in DMF (20 ml).

Sources & evidence

ORD record
ord-fa2c4ee2700c4611a76bc1b80bdf6e61
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08822530B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes