Triethylamine → 4-[(E)-2-(4'-chlorobiphenyl-4-ylcarbamoyl)vinyl]benzyl Methanesulfonate

HRID 735175

Reaction equation

HRID 735175 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][OH:25])=[CH:20][CH:19]=3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl.O>[CH3:34][S:35]([O:25][CH2:24][C:21]1[CH:20]=[CH:19][C:18](/[CH:17]=[CH:16]/[C:15](=[O:26])[NH:14][C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[CH:13][CH:12]=2)=[CH:23][CH:22]=1)(=[O:37])=[O:36]

Participants

6

Reactant 3

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

Product 1

HCID 866018934-[(E)-2-(4'-chlorobiphenyl-4-ylcarbamoyl)vinyl]benzyl Methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2.3 g (6.3 mmol) of (E)-N-(4′-chlorobiphenyl-4-yl)-3-(4-hydroxymethylphenyl)acrylamide in 200 mL of dichloromethane is combined with 1.94 mL (13.9 mmol) of triethylamine and then with 0.54 mL (6.92 mmol) of methanesulfonic acid chloride. The reaction mixture is stirred for 18 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: 1.85 g (67% of theory); C23H20ClN04S (M=441.93); calc.: molecular ion peak (M+H)+: 442/444 (Cl); found: molecular ion peak (M+H)+: 442/444 (Cl); Rf value: 0.73 (silica gel, dichloromethane/methanol/ammonia (90:10:1)).

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-9ffee921ed6949c9abd0d5ee342f198d
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Linked notes

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