Hydrochloric Acid → 3-[(4-Cyanopyridin-2-YL)sulfanyl]benzoic acid

HRID 2266993ノート

反応式

HRID 2266993 の反応式
[H-].[Na+].[SH:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].Cl[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][N:21]=1)[C:17]#[N:18].Cl>CN(C)C=O>[C:17]([C:16]1[CH:19]=[CH:20][N:21]=[C:14]([S:3][C:4]2[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=2)[C:7]([OH:9])=[O:8])[CH:15]=1)#[N:18]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 95737Benzoic acid, 3-mercapto-HCID 5686382-Chloro-4-cyanopyridine

生成物 1

HCID 573554593-[(4-Cyanopyridin-2-YL)sulfanyl]benzoic acid収率 50%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

Add sodium hydride (60% dispersion in mineral oil, 635 mg, 15.88 mmol) to a solution of 3-mercapto-benzoic acid (1.11 g, 7.22 mmol) in dimethylformamide (50 mL) chilled to 0° C. and stir. After 10 minutes add 2-chloro-isonicotinonitrile (1.00 g, 7.22 mmol). Warm gradually to ambient temperature. After 18 hours, add 1N aqueous hydrochloric acid (200 mL). Filter the resulting precipitate, washing with water and hexanes to yield the title compound as a tan solid (920 mg, 50%): 1H NMR (DMSO-d6) δ 7.62-7.66 (m, 3H), 7.84 (d, 1H), 8.03-8.08 (m, 2H), 8.62 (d, 1H), 13.26 (bs, 1H).

後処理

  1. temperatureWarm gradually to ambient temperature
  2. filtrationFilter the resulting precipitate
  3. washwashing with water and hexanes

出典と根拠

ORDレコード
ord-5da088957feb4c6f9393d2d79fae43c3
出典データセット
uspto-grants-2010_12
特許番号
US07858646B2

反応ノート

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