Chloroacetonitrile → HCID 20345057, compound

HRID 2049339Notes

Reaction equation

HRID 2049339 reaction equation
[C:1](=[S:12])([S-:11])[S:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.[K+].Cl[CH2:15][C:16]#[N:17]>>[C:1](=[S:11])([S:12][CH2:15][C:16]#[N:17])[S:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 7856ChloroacetonitrileHCID 23720344HCID 23720344, compound2×

Product 1

HCID 20345057HCID 20345057, compound

Procedure

The reaction mixture from Example 1 containing potassium p-chlorobenzyl trithiocarbonate is stirred for 0.5 hours and 12.9 ml (200 mmol) of chloroacetonitrile is then added. The temperature of the reaction mixture is adjusted to 20° to 25° C. and stirring is continued for 2 hours. The yellow color from the aqueous layer transfers to the toluene layer and the toluene layer is then separated therefrom, washed with water, brine and dried with Na2SO4. The mixture is filtered and concentrated. The residue is taken up in ether-hexane, reduced in volume and crystallized in a freezer. Recrystallization of this material from ether-hexane gives 28.5 g of p-chlorobenzyl cyanomethyl trithiocarbonate, m.p. 41°-43° C.

Workup

  1. customis adjusted to 20° to 25° C.
  2. customThe yellow color from the aqueous layer transfers to the toluene layer and the toluene layer is then separated
  3. washwashed with water, brine
  4. dry with materialdried with Na2SO4
  5. filtrationThe mixture is filtered
  6. concentrationconcentrated
  7. customcrystallized in a freezer
  8. customRecrystallization of this material from ether-hexane

Sources & evidence

ORD record
ord-4844afdf991a4821a6992d85b43ea2de
Source dataset
uspto-grants-1980_04
Patent number
US04197311

Reaction notes

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