Carbon Disulfide → HCID 86612043, compound

HRID 2055767Notes

Reaction equation

HRID 2055767 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[Mg]Br.[C:13](=[S:15])=[S:14].Br[CH:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:18]#[N:19]>O>[C:1]1([C:13]([S:15][CH:17]([C:18]#[N:19])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[S:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 22044Bromobenzyl CyanideHCID 178418423HCID 178418423, compound

Product 1

HCID 86612043HCID 86612043, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 ml round bottom flask was added 20 ml 2-naphthylmagnesium bromide (0.5M solution in THF). 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 (10:3 mixture of hexane and ethyl ether), pure α-cyanobenzyl dithionaphthalate was obtained as an orange odorless solid (63% yield). Proton and carbon NMR spectra were consistent with the expected structure, CTA-CP-2.

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 (10:3 mixture of hexane and ethyl ether)

Sources & evidence

ORD record
ord-6df41bc16a104440a1a018e2575d842b
Source dataset
uspto-grants-2008_02
Patent number
US07332552B2

Reaction notes

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