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

HRID 565860Notes

Reaction equation

HRID 565860 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-8e233144d005475c9060e002598bb750
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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