Triethylamine → 4-[(4-prop-1-ynylphenylcarbamoyl)ethynyl]benzyl Methanesulfonate

HRID 734994노트

반응식

HRID 734994 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:27])[C:17]#[C:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][OH:26])=[CH:21][CH:20]=2)=[CH:11][CH:10]=1)#[C:7][CH3:8].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:26][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([C:18]#[C:17][C:16](=[O:27])[NH:15][C:12]2[CH:11]=[CH:10][C:9]([C:6]#[C:7][CH3:8])=[CH:14][CH:13]=2)=[CH:24][CH:23]=1)(=[O:4])=[O:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 688177323-(4-Hydroxymethylphenyl)propynoic acid (4-prop-1-ynylphenyl)amide

생성물 1

HCID 866018854-[(4-prop-1-ynylphenylcarbamoyl)ethynyl]benzyl Methanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

0.14 mL (1.8 mmol) of methanesulfonic acid chloride is slowly added dropwise at ambient temperature to a solution of 0.5 g (1.72 mmol) of 3-(4-hydroxymethylphenyl)propynoic acid (4-prop-1-ynylphenyl)amide and 0.49 mL (3.6 mmol) of triethylamine in 20 mL of dichloromethane and the reaction mixture is stirred for 2 hours at ambient temperature. It is extracted three times with water and the organic phase is dried over sodium sulfate. The solvent is distilled off and the residue is stirred with diisopropyl ether. Yield: 0.48 g (75.6% of theory); C20H17NO4S (M=367.42); calc.: molecular ion peak (M+H)+: 368; found: molecular ion peak (M+H)+: 368; Rf value: 0.48 (silica gel, dichloromethane/ethanol (20:1)).

후처리

  1. extractionIt is extracted three times with water
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. distillationThe solvent is distilled off
  4. stirringthe residue is stirred with diisopropyl ether

출처 및 근거

ORD 기록
ord-4823602759d3436084441dec45c9c3b3
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592373B2

반응 노트

불러오는 중…