3-Chloro-6-hydroxyacetophenone → N-[(E)-1-(5-chloro-2-hydroxyphenyl)ethylideneamino]-3-pyrrolidin-1-ylsulfonylbenzamide

HRID 1777053ノート

反応式

HRID 1777053 の反応式
[N:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([NH:14][NH2:15])=[O:13])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([OH:29])=[C:24]([C:26](=O)[CH3:27])[CH:25]=1>CO.C(O)(=O)C>[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([OH:29])=[C:24](/[C:26](=[N:15]/[NH:14][C:12](=[O:13])[C:11]2[CH:16]=[CH:17][CH:18]=[C:9]([S:6]([N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)(=[O:7])=[O:8])[CH:10]=2)/[CH3:27])[CH:25]=1

参加物

5

反応物 2

HCID 740613-Chloro-6-hydroxyacetophenoneHCID 23180693-(Pyrrolidine-1-sulfonyl)benzohydrazide

生成物 1

HCID 136265202N-[(E)-1-(5-chloro-2-hydroxyphenyl)ethylideneamino]-3-pyrrolidin-1-ylsulfonylbenzamide収率 41.8%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

反応条件

温度
120 °C

実験手順

3-(pyrrolidin-1-ylsulfonyl)benzohydrazide (105 mg, 0.390 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (66.5 mg, 0.390 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 title compound (E)-N′-(1-(5-chloro-2-hydroxyphenyl)ethylidene)-3-(pyrrolidin-1-ylsulfonyl)benzohydrazide (70 mg, 0.163 mmol, 41.7% yield) as a solid. 1H NMR (CDCl3, 400 MHz): δ 8.18 (m, 1H), 8.13 (m, 1H), 7.95 (d, 1H, J=7.6 Hz), 7.65 (t, 1H, J=7.6 Hz), 7.41 (m, 1H), 7.21 (m, 1H), 6.93 (d, 1H, J=8.8 Hz), 3.23 (m, 4H), 2.39 (s, 3H), 1.75 (m, 4H). Mass [M+H]+: 422.1

後処理

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

出典と根拠

ORDレコード
ord-7e81cfe5321e46bbbc5e7932239de343
出典データセット
uspto-grants-2016_02
特許番号
US09266838B2

反応ノート

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