Diethyl Ether → S-(alpha-Ethyl-alpha-methylbenzylthio)methyl O,O-Diethyl Phosphorodithioate

HRID 1974248Notes

Reaction equation

HRID 1974248 reaction equation
[CH2:1]([C:3]([S:11][CH2:12]Cl)([CH3:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].P([S-])(=S)([O-])[O-].[P:19]([SH:27])([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])=[S:20].CCOCC>C(N(CC)CC)C>[P:19]([S:27][CH2:12][S:11][C:3]([CH2:1][CH3:2])([CH3:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[S:20])([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 9274O,O-Diethyl dithiophosphateHCID 177047PhosphorodithioateHCID 21489068{2-[(Chloromethyl)sulfanyl]butan-2-yl}benzene

Product 1

HCID 21489063S-(alpha-Ethyl-alpha-methylbenzylthio)methyl O,O-Diethyl Phosphorodithioate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
25 °C

Procedure

To 0.091 mole of chloromethyl α-ethyl-α-methylbenzyl sulfide and 16.9 grams (0.091 mole) of the phosphorodithioate of the formula (C2H5O)2PSSH in 100 ml. of ether is added 9.2 grams of triethylamine, dropwise, maintaining the temperature at 25° C. The mixture is stirred for several hours and then washed with water and 5% sodium hydroxide solution. Evaporation of the solvent from the dried (magnesium sulfate) solution gives 31.3 grams (95%) of a colorless liqiuid. This material is chromatographically purified on a silica gel dry-column using 10 volume percent methylene chloride in hexane as the eluant.

Workup

  1. washwashed with water and 5% sodium hydroxide solution
  2. customEvaporation of the solvent from the
  3. dry with materialdried (magnesium sulfate) solution
  4. customgives 31.3 grams (95%) of a colorless liqiuid
  5. customThis material is chromatographically purified on a silica gel dry-column

Sources & evidence

ORD record
ord-217eb2fe4acb4827a7561177655b787a
Source dataset
uspto-grants-1976_12
Patent number
US04000269

Reaction notes

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