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3-Chloro-6-hydroxyacetophenone → HCID 136265205、化合物

HRID 877648
ノート
印刷プレビュー

反応式

HRID 877648 の反応式
[NH:1]([C:3]([C:5]1[CH:6]=[C:7]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)=[O:4])[NH2:2].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([OH:25])=[C:20]([C:22](=O)[CH3:23])[CH:21]=1>CO.C(O)(=O)C>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([OH:25])=[C:20](/[C:22](=[N:2]/[NH:1][C:3]([C:5]2[CH:6]=[C:7]([S:11]([NH2:14])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=2)=[O:4])/[CH3:23])[CH:21]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 740613-Chloro-6-hydroxyacetophenoneHCID 71258151HCID 71258151、化合物

生成物 1

HCID 136265205HCID 136265205、化合物収率 40.5%

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-(hydrazinecarbonyl)benzenesulfonamide (50 mg, 0.232 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (39.6 mg, 0.232 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)-3-(2-(1-(5-chloro-2-hydroxyphenyl)ethylidene)hydrazinecarbonyl)benzenesulfonamide (36 mg, 0.094 mmol, 40.4% yield) as a solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.34 (s, 1H), 8.15 (d, 1H, J=7.6 Hz), 8.02 (d, 1H, J=7.6 Hz), 7.73 (t, 1H, J=8.0 Hz), 7.64 (m, 1H), 7.51 (bs, 2H), 7.32 (dd, 1H, J=2.4 & 8.4 Hz), 6.92 (d, 1H, J=8.4 Hz), 2.49 (s, 3H). Mass [M+H]+:368.0

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-c3df25b671d944c4a6ee19fcaf2bf997
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987335B2

反応ノート

読み込み中…

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