Chloroacetonitrile → HCID 20310736, compound

HRID 1763559Notes

Reaction equation

HRID 1763559 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]#[N:22]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:20][C:21]#[N:22])=[C:4]([CH:3]=1)[NH:9][C:10](=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 952582-Acetylamino-4-chlorophenol

Product 1

HCID 20310736HCID 20310736, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 25.0 grams of 4-chloro 2-acetamidophenol (0.135 mole) in 500 ml of acetone is added 18.7 grams of potassium carbonate (0.135 mole). To the resulting suspension is added 10.20 grams of chloroacetonitrile (0.135 mole). The suspension is stirred for 48 hours at reflux. The reaction mixture is then filtered and the solvent removed under reduced pressure to yield a dark solid residue. Recrystallization of the residue from methylene chloride-petroleum ether (1:1) followed by recrystallization twice more from methanol yields refined 5'-chloro 2'-(cyanomethoxy) acetanilide mp; 146°-149° C.

Workup

  1. temperatureat reflux
  2. filtrationThe reaction mixture is then filtered
  3. customthe solvent removed under reduced pressure
  4. customto yield a dark solid residue
  5. customRecrystallization of the residue from methylene chloride-petroleum ether (1:1)
  6. customfollowed by recrystallization twice more from methanol

Sources & evidence

ORD record
ord-d7d2d2c435174c7fbe01028f57720e73
Source dataset
uspto-grants-1978_09
Patent number
US04112117

Reaction notes

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