Triethylamine → (E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide

HRID 735172Notes

Reaction equation

HRID 735172 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.CS([Cl:38])(=O)=O>ClCCl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]3[CH:23]=[CH:22][C:21]([CH2:24][Cl:38])=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68819611(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-hydroxymethylphenyl)acrylamide

Product 1

HCID 68816418(E)-N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)acrylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2.1 g (5.77 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-hydroxymethylphenyl)acrylamide in 100 mL of dichloromethane is combined with 1.7 mL (12.19 mmol) of triethylamine and then combined with 0.46 mL (5.88 mmol) of methanesulfonic acid chloride. The reaction mixture is stirred for 3 hours at ambient temperature, diluted with water, and extracted several times with dichloromethane. The combined organic phases are dried over sodium sulfate, filtered through silica gel, and the filtrate is evaporated down. Yield: 0.4 g (18.1% of theory); C22H17Cl2NO (M=382.29); calc.: molecular ion peak (M+H)+: 381/383/385; found: molecular ion peak (M+H)+: 381/383/385.

Workup

  1. extractionextracted several times with dichloromethane
  2. dry with materialThe combined organic phases are dried over sodium sulfate
  3. filtrationfiltered through silica gel
  4. customthe filtrate is evaporated down

Sources & evidence

ORD record
ord-f8b38b86834c44ed9354a5f963b8867a
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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