Benzoyl chloride → S-tert-Butyl benzenecarbothioate

HRID 2236047Notes

Reaction equation

HRID 2236047 reaction equation
C(S)(C)(C)C.[C:6]([S:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(Cl)(=O)C1C=CC=CC=1>N1C=CC=CC=1>[C:6]([S:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 86594189HCID 86594189, compound

Product 1

HCID 12492106S-tert-Butyl benzenecarbothioateYield 50.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

S-t-butyl thiobenzoate t-Butyl mercaptan (6.15 g, 0.068 mol) was added dropwise to a solution of benzoyl chloride (10.5 g, 0.075 mol) in pyridine (6 g). The resulting mixture was allowed to stir for two hours at room temperature then poured onto ice-water and the mixture extracted with diethyl ether. The organic extract was washed with dilute HCl, water and brine and finally dried over anhydrous sodium sulfate. After removal of solvent and vacuum distillation, S-t-butyl thiobenzoate was obtained (6.64 g, 50.1% yield), b.p. 86° C. (0.8 mmHg). 1H-nmr (CDCl3) d (ppm): 1.60 (s, 9H, 3×CH3), 7.41 (m, 2H, ArH), 7.54 (m, 1H, ArH) and 7.94 (d, 2H, ArH). 13C-nmr (CDCl3) d (ppm): 29.8, 48.0, 126.8, 128.3, 132.7, 138.6 and 192.9. ii) t-Butyl Dithiobenzoate

Workup

  1. additionthen poured onto ice-water
  2. extractionthe mixture extracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with dilute HCl, water and brine
  5. dry with materialfinally dried over anhydrous sodium sulfate
  6. customAfter removal of solvent and vacuum distillation

Sources & evidence

ORD record
ord-da8bbb38f5a8496484dd9d37530c91b9
Source dataset
uspto-grants-2010_05
Patent number
US07714075B1

Reaction notes

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