Benzo(d)thiazol-2-amine → 2,2,3,3-Tetramethylcyclopropanecarboxylic acid benzothiazol-2-ylamide

HRID 78407

反応式

HRID 78407 の反応式
[CH3:1][C:2]1([CH3:10])[C:4]([CH3:6])([CH3:5])[CH:3]1[C:7]([OH:9])=O.[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[NH2:20]>>[S:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[NH:20][C:7]([CH:3]1[C:4]([CH3:5])([CH3:6])[C:2]1([CH3:1])[CH3:10])=[O:9]

参加物

3

反応物 2

HCID 8706Benzo(d)thiazol-2-amineHCID 1521152,2,3,3-Tetramethylcyclopropanecarboxylic acid

生成物 1

HCID 240558432,2,3,3-Tetramethylcyclopropanecarboxylic acid benzothiazol-2-ylamide収率 27.1%

実験手順

A mixture of 2,2,3,3-tetramethylcyclopropanecarboxylic acid (0.50 g, 3.5 mmol) and benzothiazol-2-ylamine (0.58 g, 3.9 mmol) were processed as in Example 9A. Purification by column chromatography (SiO2, 20-40% ethyl acetate/hexanes gradient) afforded 0.26 g (27%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ ppm 1.22-1.27 (m, 6H), 1.36 (s, 6H), 1.67 (s, 1H), 2.07-2.18 (m, 2H), 3.34 (s, 3H), 3.41 (t, J=5.8 Hz, 2H), 4.39-4.53 (m, 2H), 7.20-7.26 (m, 1H), 7.37-7.42 (m, 2H), 7.60 (d, J=7.5 Hz, 1H); MS (DCI/NH3) m/z 275 (M+H)+.

後処理

  1. customPurification by column chromatography (SiO2, 20-40% ethyl acetate/hexanes gradient)

出典と根拠

ORDレコード
ord-bba11dce68a24fc2b23f79f509d26f99
出典データセット
uspto-grants-2014_09
特許番号
US08841334B2

関連ノート

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