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

HRID 734994ノート

反応式

HRID 734994 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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)).

後処理

  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

出典と根拠

ORDレコード
ord-4823602759d3436084441dec45c9c3b3
出典データセット
uspto-grants-2009_09
特許番号
US07592373B2

反応ノート

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