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

HRID 2266994노트

반응식

HRID 2266994 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: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]

참가 물질

6

반응물 4

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

생성물 1

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

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 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).

후처리

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

출처 및 근거

ORD 기록
ord-07b93c78d4494607a739c9ed84f4e433
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858646B2

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