Chloroacetonitrile → Methyl 2-[(Cyanomethyl)thio]benzoate

HRID 1388314Notes

Reaction equation

HRID 1388314 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].C[O-].[Na+].Cl[CH2:16][C:17]#[N:18]>CO>[C:1]([C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[S:4][CH2:16][C:17]#[N:18])([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 21009Benzoic acid, 2-mercapto-, methyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 2778417Methyl 2-[(Cyanomethyl)thio]benzoateYield 69.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of methyl thiosalicylate (164 g, 0.975 mol) in methanol (1.1 L) was added in one portion to a cold solution of freshly prepared sodium methoxide (from 25.5 g, 1.1 mol Na-metal in methanol, 1.1 L). The salt solution was cooled to 0° C. and a cold (0° C.) solution of chloroacetonitrile (83.7 g, 1.1 mol) in methanol (0.5 L) was added in one portion with stirring. After several minutes a strong precipitate appeared. After standing for several days at room temperature, the precipitate was collected, washed with ice-cold methanol, then washed well with water and dried to give 141.0 g of 2-(2-carbomethoxyphenylthio)acetonitrile, mp 120°-122° C. [described by K. Gorlitzer, Arch. Pharmaz., 308, 700 (1975)].

Workup

  1. waitAfter several minutes a strong precipitate appeared
  2. waitAfter standing for several days at room temperature
  3. customthe precipitate was collected
  4. washwashed with ice-cold methanol
  5. washwashed well with water
  6. customdried

Sources & evidence

ORD record
ord-6833f7f858ef4000a3c0d2f1a3307dee
Source dataset
uspto-grants-1984_02
Patent number
US04431657

Reaction notes

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