Benzylamine → N-[4-(Methylthio)phenyl]benzenemethanamine

HRID 984674Notes

Reaction equation

HRID 984674 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([NH:17][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[CH:4][CH:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 660374-Bromothioanisole

Product 1

HCID 9964622N-[4-(Methylthio)phenyl]benzenemethanamineYield 88%

Procedure

Using the general procedure, 4-bromothioanisole (203 mg, 1.0 mmol) was coupled with benzylamine (164 μL, 1.5 mmol). Purification of the crude product by column chromatography on silica gel using hexane/ethyl acetate (15:1) as eluent afforded the desired product as a white solid (201 mg, 88% yield). Rf=0.4 (hexane/ethyl acetate=10:1).

Workup

  1. customPurification of the crude product by column chromatography on silica gel

Sources & evidence

ORD record
ord-a5a87c535263438ca18bce494f1ecc2e
Source dataset
uspto-grants-2005_03
Patent number
US06867298B2

Reaction notes

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