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

HRID 2266994Notes

Reaction equation

HRID 2266994 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-07b93c78d4494607a739c9ed84f4e433
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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