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

HRID 1277039Notes

Reaction equation

HRID 1277039 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 acetatediisopropylether 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 acetatediisopropylether

Sources & evidence

ORD record
ord-5c218cab46634052bf7c8d4f37cb8461
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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