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

HRID 735175노트

반응식

HRID 735175 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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)).

후처리

  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

출처 및 근거

ORD 기록
ord-9ffee921ed6949c9abd0d5ee342f198d
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592373B2

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