Phenylmethanesulfonyl chloride → HCID 61401001, compound

HRID 1505611Notes

Reaction equation

HRID 1505611 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:19]1([CH2:25][S:26](Cl)(=[O:28])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][S:26]([CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:28])=[O:27])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 74740Phenylmethanesulfonyl chlorideHCID 775714-BromobenzylamineHCID 81531Diisopropylethylamine

Product 1

HCID 61401001HCID 61401001, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-bromophenyl)methanamine (2.5 g, 13 mmol) in dichloromethane (45 mL) was added N,N-diisopropylethylamine (3.5 mL, 20 mmol), followed by phenylmethanesulfonyl chloride (3.1 g, 16 mmol) and the reaction was stirred at ambient temperature for 1 hour. The precipitate was then collected by filtration, washed with dichloromethane and dried under reduced pressure to give N-[(4-bromophenyl)methyl]-1-phenyl-methanesulfonamide (2.79 g, 61% yield). LCMS (m/z) ES+ 340.0 [M+1]+.

Workup

  1. filtrationThe precipitate was then collected by filtration
  2. washwashed with dichloromethane
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-20143890bdef4f5d98a6c8b9f86f16f9
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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