1-(5-Chloro-2-nitrophenyl)ethanone → N-[(E)-1-(5-chloro-2-nitrophenyl)ethylideneamino]-3-morpholin-4-ylsulfonylbenzamide

HRID 1777057

反応式

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[O:14]1[CH2:19][CH2:18][N:17]([S:20]([C:23]2[CH:24]=[C:25]([CH:30]=[CH:31][CH:32]=2)[C:26]([NH:28][NH2:29])=[O:27])(=[O:22])=[O:21])[CH2:16][CH2:15]1>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6](/[C:8](=[N:29]/[NH:28][C:26](=[O:27])[C:25]2[CH:30]=[CH:31][CH:32]=[C:23]([S:20]([N:17]3[CH2:18][CH2:19][O:14][CH2:15][CH2:16]3)(=[O:21])=[O:22])[CH:24]=2)/[CH3:9])[CH:7]=1

参加物

反応条件

温度: 120 °C

実験手順

1-(5-chloro-2-nitrophenyl)ethanone (30 mg, 0.150 mmol) and 3-(morpholinosulfonyl)benzohydrazide (42.9 mg, 0.150 mmol) was dissolved in Methanol (Volume: 4 ml) in the presence of acetic acid as a catalyst and then the reaction mixture was heated via microwave irradiation to 120° C. for 30 min. Reaction was monitored by TLC. After completion of the reaction, following cooling, the solvent was removed by vacuum and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2), afforded the product (E)-N′-(1-(5-chloro-2-nitrophenyl)ethylidene)-3-(morpholinosulfonyl)benzohydrazide (15 mg, 0.030 mmol, 20.09% yield) as a solid. 1H NMR (CDCl3, 400 MHz): δ 8.20 (m, 1H), 8.07 (m, 1H), 7.88 (m, 1H), 7.66 (m, 1H), 7.51 (m, 2H), 7.39 (m, 1H), 3.69 (m, 4H), 2.99 (m, 4H), 2.29 (s, 3H). Mass [M+H]+: 468.0

後処理

customReaction
customAfter completion of the reaction
temperaturefollowing cooling
customthe solvent was removed by vacuum
customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

出典と根拠

ORDレコード: ord-56888b1368ca4463adac491dc577b144
出典データセット: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09266838B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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