Methanesulfonyl chloride → (E)-N-[4-(chloromethyl)phenyl]3-(4-methylphenyl)cinnamamide

HRID 2228058Notes

Reaction equation

HRID 2228058 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:5][CH:4]=1.[Cl-].[Li+].CS([Cl:33])(=O)=O.C(OC(=O)C)C.Cl>ClCCl.C(N(CC)CC)C>[Cl:33][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 18472511(E)-N-[4-(hydroxymethyl)phenyl]-3-(4-methylphenyl)cinnamamideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 18472214(E)-N-[4-(chloromethyl)phenyl]3-(4-methylphenyl)cinnamamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of (E)-N-[4—(hydroxymethyl)phenyl]-3—(4-methylphenyl)cinnamamide (3.00 g), lithium chloride (741 mg), triethylamine (3.06 ml), DMAP(catalytic amount) and dichloro-methane (300 ml) was added methanesulfonyl chloride (1.15 ml), and the mixture was stirred at room temperature for 13 hours. To the reaction mixture was added 4N hydrochloric acid ethyl acetate solution (3.3 ml), and the mixture was purified with column chromatography (ethyl acetate) and recrystallized from ethyl acetate-diisopropylether to give (E)-N-[4—(chloromethyl)phenyl]-3—(4-methylphenyl)cinnamamide (2.00 g) as colorless crystals.

Workup

  1. customthe mixture was purified with column chromatography (ethyl acetate)
  2. customrecrystallized from ethyl acetate-diisopropylether

Sources & evidence

ORD record
ord-cfc866a9fd954e43a43db55cf56b834d
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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