Water → HCID 23350146, compound

HRID 2058249Notes

Reaction equation

HRID 2058249 reaction equation
O.[C:2](=[S:8])([S-:7])[S:3][CH:4]([CH3:6])[CH3:5].[K+].Cl[CH2:11][C:12]#[N:13]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:2](=[S:7])([S:8][CH2:11][C:12]#[N:13])[S:3][CH:4]([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 962WaterHCID 7856ChloroacetonitrileHCID 23699753HCID 23699753, compound

Product 1

HCID 23350146HCID 23350146, compoundYield 59.6%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

To a two phase system containing 100 ml of water, 100 ml of toluene, 19.0 g (100 mmol) of potassium isopropyl trithiocarbonate and 50 mg of tetrabutyl ammonium bisulfate, a phase transfer catalyst, is added 6.3 ml (100 mmol) of chloroacetonitrile. The temperature of the reaction is maintained at between 20° and 30° C. After 4.5 hours the layers are separated and the toluene layer washed with water, brine, dried with Na2SO4, filtered, and concentrated in vacuo. The residue is distilled to give 11.4 g of isopropyl cyanomethyl trithiocarbonate as a yellow oil, boiling point 110°-113° C. at 0.1 mm Hg.

Workup

  1. temperatureThe temperature of the reaction is maintained at between 20° and 30° C
  2. customAfter 4.5 hours the layers are separated
  3. washthe toluene layer washed with water, brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. distillationThe residue is distilled

Sources & evidence

ORD record
ord-3b3acc01222d4aed99876ce4b6918d86
Source dataset
uspto-grants-1980_07
Patent number
US04215140

Reaction notes

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