Benzyl mercaptan → 2,4-Bis(benzylsulfanyl)-1,3,2lambda~5~,4lambda~5~-dithiadiphosphetane-2,4-dithione

HRID 2181287Notes

Reaction equation

HRID 2181287 reaction equation
[S].P12([S:14][P:12]3([S:15]P(S[P:8]([S:11]3)([S:10]1)=[S:9])(=S)S2)=[S:13])=S.[CH:16]1[CH:21]=[CH:20][C:19]([CH2:22]S)=[CH:18][CH:17]=1>C1C(Cl)=CC=C(Cl)C=1>[CH2:22]([S:10][P:8]1(=[S:9])[S:11][P:12]([S:14][CH2:22][C:19]2[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=2)(=[S:13])[S:15]1)[C:19]1[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7509Benzyl mercaptanHCID 14817Phosphorus sulfide (P2S5)2×HCID 5362487Sulfur

Product 1

HCID 224858202,4-Bis(benzylsulfanyl)-1,3,2lambda~5~,4lambda~5~-dithiadiphosphetane-2,4-dithioneYield 50%

Reagents, catalysts & solvents 1

HCID 46851,4-DichlorobenzeneSolvent

Conditions

Temperature
190 °C

Procedure

The method is derived from the reference H. Davy, Sulfur Letters, vol. 3(2) 39, (1985). P4S10 (8.88 g, 0.02 mol) is mixed with 30 ml of dichlorobenzene until this solvent refluxes (160° C.). Benzylthiol (16.5 ml; 0.14 mol) is slowly added to the solution over 40 minutes, while increasing the temperature up to 190° C. The solution becomes clear; the reaction temperature is then reduced to 80° C. The stirring is stopped in order to allow the residual P4S10 to be separated by settling. The solution is filtered in the hot state. The product crystallizes slowly after filtration. The yield is 50%.

Workup

  1. custom(160° C.)
  2. customis then reduced to 80° C
  3. customto be separated
  4. filtrationThe solution is filtered in the hot state
  5. customThe product crystallizes slowly
  6. filtrationafter filtration

Sources & evidence

ORD record
ord-b47902b3e83446419b0d62d423f1baf4
Source dataset
uspto-grants-2005_05
Patent number
US06890980B2

Reaction notes

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