Carbon Disulfide → alpha-Cyanobenzyl 4-methoxydithiobenzoate

HRID 2055768Notes

Reaction equation

HRID 2055768 reaction equation
C([Mg]Br)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:12](=[S:14])=[S:13].Br[CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:17]#[N:18]>O>[CH3:9][O:8][C:5]1[CH:4]=[CH:3][C:2]([C:12]([S:14][CH:16]([C:17]#[N:18])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[S:13])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 22044Bromobenzyl CyanideHCID 178418276HCID 178418276, compound

Product 1

HCID 58856299alpha-Cyanobenzyl 4-methoxydithiobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 ml round bottom flask was added 20 ml p-anisylmagnesium bromide (0.49M solution in ethyl ether). 0.76 g carbon disulfide was added dropwise to this mixture and stirred for ½ h at room temperature. Then to the dark red solution was added 2 g α-bromobenzeneacetonitrile dropwise and the mixture stirred for another 2 h. Water was added to the mixture and the organic product was extracted with diethyl ether (3×50 ml), dried with magnesium sulfate overnight and filtered. After removal of solvent and column chromatography (5:1 mixture of hexane and ethyl ether), pure α-cyanobenzyl 4-methoxydithiobenzoate was obtained as an orange odorless solid (73% yield). Proton and carbon NMR spectra were consistent with the expected structure, CTA-CP-3.

Workup

  1. stirringthe mixture stirred for another 2 h
  2. extractionthe organic product was extracted with diethyl ether (3×50 ml)
  3. dry with materialdried with magnesium sulfate overnight
  4. filtrationfiltered
  5. customAfter removal of solvent and column chromatography (5:1 mixture of hexane and ethyl ether)

Sources & evidence

ORD record
ord-fb273ca128584b54bc3d890d6ac61f47
Source dataset
uspto-grants-2008_02
Patent number
US07332552B2

Reaction notes

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