Chloroacetonitrile → HCID 12286867, compound

HRID 1414015Notes

Reaction equation

HRID 1414015 reaction equation
C[O-].[Na+].[C:4]([OH:12])(=[S:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl[CH2:14][C:15]#[N:16]>C1COCC1.CCOCC>[C:4]([S:11][CH2:14][C:15]#[N:16])(=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 7856ChloroacetonitrileHCID 10942334Sodium MethoxideHCID 178526132HCID 178526132, compound

Product 1

HCID 12286867HCID 12286867, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium methoxide (5.13 g; 0.095 mol) is added with stirring to an ice cold solution of thiobenzoic acid (13.8 g; 0.095 mol) in THF (100 ml). A yellow slurry forms. Next, chloroacetonitrile (6.45 ml; 0.10 mol) is added, and the reaction mixture stirred overnight at room temperature. It is then filtered, and the filtrate concentrated in vacuo to yield a yellow oil. This oil is dissolved in ether, the solution washed with saturated sodium bicarbonate solution, saturated salt solution, dried over sodium sulfate and concentrated in vacuo. The residual oil is distilled (boiling point 105°-106° C. at 10.5 mm) to afford 12.8 g (76%) of title product, a yellow oil.

Workup

  1. filtrationIt is then filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto yield a yellow oil
  4. washthe solution washed with saturated sodium bicarbonate solution, saturated salt solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. distillationThe residual oil is distilled (boiling point 105°-106° C. at 10.5 mm)

Sources & evidence

ORD record
ord-8ea1a4c42b5549faa44bd4e8d55f3d55
Source dataset
uspto-grants-1981_02
Patent number
US04252814

Reaction notes

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