Diethyl Ether → S-Benzyl O-phenyl carbonodithioate

HRID 479091Notes

Reaction equation

HRID 479091 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[CH:11]1[CH:16]=[CH:15][C:14]([O:17][C:18](Cl)=[S:19])=[CH:13][CH:12]=1.C(OCC)C>O>[O:17]([C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1)[C:18]([S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[S:19]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 70498Phenyl thioxochloroformate

Product 1

HCID 190260S-Benzyl O-phenyl carbonodithioateYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Benzyl mercaptan (1.24 g, 10 mmol) was added to an aqueous (20 mL) solution of NaOH (0.8 g, 20 mmol) at room temperature and stirred for 15 minutes. Phenyl thionochloroformate (2.07 g, 12 mmol) was next added dropwise to this solution at the same temperature and stirred for a further 2 hours. Diethyl ether (20 mL) and water (50 mL) was added and the organic layer separated. The aqueous layer was extracted with diethyl ether (3×20 mL). The combined organic fractions were dried with Na2SO4, filtered, the solvent removed and the crude product chromatographed (using silica gel, 2% ethyl acetate in petroleum spirits) to afford the title compound (1.95 g, 75%) as a yellow oil. 1H-nmr (CDCl3) δ 4.43 (2H), 7.10-7.50 (10H). 13C-nmr (CDCl3) δ 41.7, 122.1, 126.7, 127.8, 128.8, 129.3, 129.6, 135.1, 154.0, 213.0.

Workup

  1. stirringstirred for a further 2 hours
  2. customthe organic layer separated
  3. extractionThe aqueous layer was extracted with diethyl ether (3×20 mL)
  4. dry with materialThe combined organic fractions were dried with Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed
  7. customthe crude product chromatographed (using silica gel, 2% ethyl acetate in petroleum spirits)

Sources & evidence

ORD record
ord-5dbf10c21b194082a200908b01af8723
Source dataset
uspto-grants-2003_11
Patent number
US06642318B1

Reaction notes

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