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Dimethylformamide → 2-Methyl hydrogen 2,3-dihydro-3-hydroxythiazolo[3,2-a]benzoimidazole-2,7-dicarboxylate

HRID 478843
ノート
印刷プレビュー

反応式

HRID 478843 の反応式
Cl[C:2](=[CH:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].CN(C=O)C.[SH:14][C:15]1[NH:16][C:17]2[CH:23]=[C:22]([C:24]([OH:26])=[O:25])[CH:21]=[CH:20][C:18]=2[N:19]=1>O>[OH:8][CH:7]1[N:19]2[C:15](=[N:16][C:17]3[CH:23]=[C:22]([C:24]([OH:26])=[O:25])[CH:21]=[CH:20][C:18]=32)[S:14][CH:2]1[C:3]([O:5][CH3:6])=[O:4]
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 6228DimethylformamideHCID 73847320Methyl 2-chloro-3-hydroxypropenoateHCID 178524147HCID 178524147、化合物

生成物 1

HCID 180030412-Methyl hydrogen 2,3-dihydro-3-hydroxythiazolo[3,2-a]benzoimidazole-2,7-dicarboxylate収率 82.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

Methyl 2-chloro-3-hydroxypropenoate (114 g) was added to DMF (460 ml) solution of 2-mercaptobenzoimidazole-5-carboxylic acid (135 g), and the mixture was stirred overnight at 60° C. After cooling to room temperature, water (3 L) was gradually added to the reaction solution and stirred. The thus precipitated crystals were collected by filtration to obtain crude crystals of 2-methyl hydrogen 2,3-dihydro-3-hydroxythiazolo[3,2-a]benzoimidazole-2,7-dicarboxylate (168 g). Next, the thus obtained crude crystals were suspended in 1,4-dioxane (1.5 L), and the suspension was mixed with 4 M HCl 1,4-dioxane solution (500 ml) and stirred at room temperature for 60 hours. The resulting precipitate was collected by filtration and washed with 1,4-dioxane to obtain crude crystals of 2-methyl hydrogen 2,3-dihydro-3-hydroxythiazolo[3,2-a]benzoimidazole-2,6-dicarboxylate hydrochloride (189 g). The thus obtained crude crystals were slowly added to concentrated sulfuric acid (750 ml) which was heated at 60° C. and stirred at the same temperature for 1 hour. After cooling to room temperature, the reaction solution was poured into ice water, and the thus precipitated crystals were collected by filtration to obtain the title compound (152 g).

後処理

  1. temperatureAfter cooling to room temperature
  2. stirringstirred
  3. filtrationThe thus precipitated crystals were collected by filtration

出典と根拠

ORDレコード
ord-d5aeb74b8bb84af5ad6047d5849d4a6e
出典データセット
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06642264B1

反応ノート

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