p-Toluenesulfonyl azide → HCID 73213267、化合物

HRID 2381784ノート

反応式

HRID 2381784 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1.S([N:28]=[N+:29]=[N-])(C1C=CC(C)=CC=1)(=O)=O>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.[OH-].[Na+]>[N:1]([C:2]1[S:3][C:4]([C:8]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:5]([CH3:7])[N:6]=1)=[N+:28]=[N-:29]

参加物

6

反応物 2

HCID 13661p-Toluenesulfonyl azideHCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

生成物 1

HCID 73213267HCID 73213267、化合物収率 63%

試薬・触媒・溶媒 3

HCID 5963Benzyltrimethylammonium chloride触媒HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

A solution of 2-amino-N-benzyl-4-methylthiazole-5-carboxamide (1.20 g, 4.86 mmol), tosyl azide (1.91 g, 9.71 mmol) and benzyl trimethylammonium chloride (0.05 g, 0.27 mmol) in dichloromethane (21 mL) and 40% aqueous sodium hydroxide solution (11 mL) was stirred at ambient temperature for 18 h. The reaction mixture was extracted with dichloromethane (100 mL). The separated organic layer was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:hexanes, 1:4) to afford the title compound (0.83 g, 63%): MS (ES−) m/z 272.2 (M−1).

後処理

  1. extractionThe reaction mixture was extracted with dichloromethane (100 mL)
  2. dry with materialThe separated organic layer was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (ethyl acetate:hexanes, 1:4)

出典と根拠

ORDレコード
ord-0fab73d4ddca403b9bd0a223381784e9
出典データセット
uspto-grants-2012_09
特許番号
US08258160B2

反応ノート

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