Hydrochloric Acid → 3-(5-Cyano-pyridin-2-ylsulfanyl)-benzoic acid

HRID 2266994ノート

反応式

HRID 2266994 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:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][N:15]=1.Cl>CN(C)C=O>[C:18]([C:17]1[CH:20]=[CH: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])=[N:15][CH:16]=1)#[N:19]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 95737Benzoic acid, 3-mercapto-HCID 51520946-Chloro-3-pyridinecarbonitrile

生成物 1

HCID 641647833-(5-Cyano-pyridin-2-ylsulfanyl)-benzoic acid収率 68%

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 6-chloro-nicotinonitrile (1.00 g, 7.22 mmol). Warm gradually to ambient temperature. After 18 hours, add 1N aqueous hydrochloric acid (200 mL). Filter resulting precipitate, washing with water and hexanes to yield the title compound as a tan solid (1.25 g, 68%): 1H NMR (DMSO-d6) δ 7.22 (d, 1H), 7.67 (t, 1H), 7.88 (dt, 1H), 8.07-8.12 (m, 3H), 8.82 (dd, 1H), 13.30 (bs, 1H).

後処理

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

出典と根拠

ORDレコード
ord-07b93c78d4494607a739c9ed84f4e433
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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