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Phosphorus oxychloride → 4-Isopropyl-thiazole-2-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide

HRID 1422529
ノート
印刷プレビュー

反応式

HRID 1422529 の反応式
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH2:10][CH:11]([O:14][CH3:15])[O:12][CH3:13])[CH:5]=[CH:4][C:3]=1[C:16](=[O:18])[CH3:17].[CH:19]([C:22]1[N:23]=[C:24]([C:27](O)=[O:28])[S:25][CH:26]=1)([CH3:21])[CH3:20].O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:16]([C:3]1[C:2]([NH:1][C:27]([C:24]2[S:25][CH:26]=[C:22]([CH:19]([CH3:21])[CH3:20])[N:23]=2)=[O:28])=[C:7]([Cl:8])[C:6]([O:9][CH2:10][CH:11]([O:12][CH3:13])[O:14][CH3:15])=[CH:5][CH:4]=1)(=[O:18])[CH3:17]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 224993072-Thiazolecarboxylic acid, 4-(1-methylethyl)-HCID 574451961-[2-Amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone

生成物 1

HCID 672246774-Isopropyl-thiazole-2-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide収率 96.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine
溶媒

反応条件

温度
-10 °C

実験手順

1-[2-amino-3-chloro-4-(2,2-dimethoxy-ethoxy)-phenyl]-ethanone (1.89 g, 6.92 mmol) and 4-isopropyl-thiazole-2-carboxylic acid (1.77 g, 10.38 mmol) was dissolved in pyridine (20 mL) and was cooled to −10° C. POCl3 (0.823 mL, 8.99 mmol) was added dropwise. The reaction was stirred at −10° C. for 2 hours. The reaction was quenched with CH3OH (5 mL). After 15 minutes, the reaction was taken up in EtOAc and extracted with 2N HCl(aq). The organic layer was dried with Na2SO4, filtered and was concentrated. 4-Isopropyl-thiazole-2-carboxylic acid [6-acetyl-2-chloro-3-(2,2-dimethoxy-ethoxy)-phenyl]-amide (2.84 g, 96%) was isolated by silica gel chromatography as a white solid.

後処理

  1. customThe reaction was quenched with CH3OH (5 mL)
  2. waitAfter 15 minutes
  3. extractionextracted with 2N HCl(aq)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationwas concentrated

出典と根拠

ORDレコード
ord-a1a00cbbf35846ec8f7960fda113f412
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927484B2

反応ノート

読み込み中…

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