Niclosamide → HCID 23966630、化合物

HRID 1509840

反応式

HRID 1509840 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[Cl:19])=[O:8].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:22]([O:21][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][C:6]=1[C:7](=[O:8])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[Cl:19])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

5

反応物 2

HCID 4477NiclosamideHCID 7412Benzoyl chloride

生成物 1

HCID 23966630HCID 23966630、化合物

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
50 °C

実験手順

A suspension of 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide (1.27 g., 3.88 mmol) in pyridine (15 mL) was treated with 4-dimethylaminopyridine (30 mg) and benzoyl chloride (0.49 mL, 4.27 mmol) was introduced dropwise. The suspension was warmed to 50° C. for one hour then cooled to room temperature and stirred for 17 hours. The reaction mixture was partitioned between 1N aqueous HCl and ethyl acetate. The ethyl acetate phase was washed with water, then brine, dried over magnesium sulfate, and concentrated to an off-white solid. This was recrystallized from ethyl acetate/hexanes. 1HNMR (500 MHz, DMSO-d6): δ7.70 (M, 3H), 7.73 (m, 2H), 7.89 (m, 1H), 7.93 (M, 1H), 8.19 (m, 1H), 8.32 (m, 1H), 10.60 (s, 1H).

後処理

  1. additionwas introduced dropwise
  2. temperaturethen cooled to room temperature
  3. customThe reaction mixture was partitioned between 1N aqueous HCl and ethyl acetate
  4. washThe ethyl acetate phase was washed with water
  5. dry with materialbrine, dried over magnesium sulfate
  6. concentrationconcentrated to an off-white solid
  7. customThis was recrystallized from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-c46173826d29412897e87d842c4660f2
出典データセット
uspto-grants-2012_07
特許番号
US08211882B2

関連ノート

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