Methanesulfonyl chloride → N-(3-chloro-4-cyanophenyl)methanesulfonamide

HRID 2246232

Reaction equation

HRID 2246232 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:10])[CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl>[Cl:10][C:4]1[CH:3]=[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 887284-Amino-2-chlorobenzonitrile

Product 1

HCID 669685N-(3-chloro-4-cyanophenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-amino-2-chlorobenzonitrile (5.02 g, 32.9 mmol) in dichloromethane (80 mL) was added N,N-diisopropylethylamine (17.0 mL, 97.8 mmol) and methanesulfonyl chloride (3.0 mL, 38.8 mmol) at −78° C. The reaction was then allowed to warm to room temperature slowly. After stirring at room temperature for 12 h, the reaction was quenched with 1 N hydrochloric acid. The organic phase was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 50:50 hexanes/ethyl acetate) to give the desired product.

Workup

  1. customthe reaction was quenched with 1 N hydrochloric acid
  2. concentrationThe organic phase was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (silica gel, 50:50 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-e2b8e8572112476fb1d7d958a2cd6615
Source dataset
uspto-grants-2010_03
Patent number
US07687492B2

Linked notes

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