Chloroacetonitrile → HCID 20345064, compound

HRID 2049341Notes

Reaction equation

HRID 2049341 reaction equation
[C:1](=[S:12])([S-:11])[S:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[K+].Cl[CH2:15][C:16]#[N:17]>O1CCCC1>[C:1](=[S:11])([S:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[S:12][CH2:15][C:16]#[N:17]

Participants

4

Reactant 2

HCID 7856ChloroacetonitrileHCID 23720343HCID 23720343, compound

Product 1

HCID 20345064HCID 20345064, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution containing 10.1 g (40 mmol) of potassium phenethyl trithiocarbonate in 100 ml of tetrahydrofuran is added 2.6 ml (40 mmol) of chloroacetonitrile while maintaining the temperature of the reaction mixture at 20°-25° C. The mixture is stirred for 1 hour and concentrated in vacuo. The residue is then taken up in ether, washed with brine, dried with Na2SO4, filtered and concentrated in vacuo. The residue is crystallized from an ether-hexane mixture to give 9.7 g of a yellow solid, cyanomethyl phenethyl trithiocarbonate, melting point 72°-73° C.

Workup

  1. temperaturewhile maintaining the temperature of the reaction mixture at 20°-25° C
  2. concentrationconcentrated in vacuo
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is crystallized from an ether-hexane mixture

Sources & evidence

ORD record
ord-cf765467a57a46e381c6313f0bf594ce
Source dataset
uspto-grants-1980_04
Patent number
US04197311

Reaction notes

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