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

HRID 2266993노트

반응식

HRID 2266993 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-5da088957feb4c6f9393d2d79fae43c3
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858646B2

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