Benzoyl chloride → s-pyridin-2-yl benzenecarbothioate

HRID 2253285Notes

Reaction equation

HRID 2253285 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1COCC1>[C:8](=[O:15])([S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 178418616HCID 178418616, compound

Product 1

HCID 264044s-pyridin-2-yl benzenecarbothioateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a standard procedure,16 a solution of 2-mercaptopyridine (3.33 g, 30.0 mmol) in THF (30 mL) was treated with benzoyl chloride (4.21 g, 30.0 mmol) at room temperature with stirring for 30 min. The standard workup followed by precipitation afforded a pale yellow solid (5.67 g, 88%): mp 48-50° C. 1H NMR spectral data are consistent with reported values:15 1H NMR δ 7.31-7.37 (m, 1H), 7.46-7.53 (m, 2H), 7.59-7.65 (m, 1H), 7.71-7.83 (m, 2H), 8.00-8.06 (m, 2H), 8.66-8.71 (m, 1H); 13C NMR δ 123.7, 127.6, 128.9, 131.0, 134.0, 136.6, 137.3, 150.6, 151.4, 189.4. Anal. Calcd for C12H9NOS: C, 66.95; H, 4.21; N, 6.51. Found: C, 66.63; H, 4.12; N, 6.57.

Workup

  1. customThe standard workup followed by precipitation

Sources & evidence

ORD record
ord-27fa0e3442184be28ef6e74778795b68
Source dataset
uspto-grants-2008_01
Patent number
US07323561B2

Reaction notes

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