Ammonia → 2-Amino-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl ester

HRID 447028ノート

反応式

HRID 447028 の反応式
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:7]=[C:6]([N+:16]([O-])=O)[C:5]=1[S:19][C:20]#[N:21].N>C(O)(=O)C.O.[Fe]>[CH3:1][O:2][C:3]([C:4]1[C:5]2[S:19][C:20]([NH2:21])=[N:16][C:6]=2[CH:7]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:9]=1)=[O:22]

参加物

6

反応物 2

HCID 222AmmoniaHCID 57813637HCID 57813637、化合物

生成物 1

HCID 578136562-Amino-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl ester収率 46.2%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

A solution of 3-Nitro-5-pyridin-3-yl-2-thiocyanato-benzoic acid methyl ester (1.1 g, 3.49 mmol) in glacial acetic acid (23 ml) was treated with iron powder (0.97 g, 17.5 mmol) and stirred at ambient temperature for 16 h. The resultant mixture was diluted with water (200 ml) and made alkaline by the addition of concentrated ammonia solution. The mixture was filtered and the filtrate extracted with ethyl acetate (3×200 ml). The filtered solid was extracted with boiling ethanol (3×250 ml) and the combined organic fractions evaporated to dryness to give 2-Amino-5-pyridin-3-yl-benzothiazole-7-carboxylic acid methyl ester as an off-white solid (0.46 g, 46%).

後処理

  1. filtrationThe mixture was filtered
  2. extractionthe filtrate extracted with ethyl acetate (3×200 ml)
  3. extractionThe filtered solid was extracted with boiling ethanol (3×250 ml)
  4. customthe combined organic fractions evaporated to dryness

出典と根拠

ORDレコード
ord-ac634b7a3f444b2bb51836f6a5567c09
出典データセット
uspto-grants-2013_07
特許番号
US08481544B2

反応ノート

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