Dimethyl Disulfide → HCID 19866712, compound

HRID 1199469Notes

Reaction equation

HRID 1199469 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH:4]=1.C([Li])CCC.[CH3:19][S:20]SC>C(OCC)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[S:10][CH:11]=[CH:12][C:13]=2[S:20][CH3:19])[CH:4]=1

Participants

6

Reactant 3

HCID 12232Dimethyl DisulfideHCID 19866740HCID 19866740, compoundHCID 178418339Butyllithium

Product 1

HCID 19866712HCID 19866712, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

The product of step (b) above (5 g) dissolved in dry diethyl ether (100 ml) was cooled to -50° and treated with butyl lithium in hexane (2.2M, 13 ml) dropwise during 0.5 hour. The mixture was warmed to -10° for 10 minutes, then cooled to -30°. Dimethyl disulphide (3.5 ml) was then added dropwise. The mixture was maintained at -30° for 0.5 hour then warmed up to room temperature during several hours. Aqueous work-up and ethyl acetate extraction gave the sub-title compound as an oil.

Workup

  1. temperaturewas cooled to -50°
  2. temperatureThe mixture was warmed to -10° for 10 minutes
  3. temperaturecooled to -30°
  4. temperatureThe mixture was maintained at -30° for 0.5 hour
  5. extractionAqueous work-up and ethyl acetate extraction

Sources & evidence

ORD record
ord-98929057995643fbaf763b36ab4d09fe
Source dataset
uspto-grants-1990_02
Patent number
US04900751

Reaction notes

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