Toluene → Trichloroacetyl isocyanate

HRID 129557Notes

Reaction equation

HRID 129557 reaction equation
[O-:1][C:2]#[N:3].[Na+].C(#N)C.C1(C)C=CC=CC=1.[Cl:15][C:16]([Cl:21])([Cl:20])[C:17](Cl)=[O:18]>O>[Cl:15][C:16]([Cl:21])([Cl:20])[C:17]([N:3]=[C:2]=[O:1])=[O:18]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6342AcetonitrileHCID 6420Trichloroacetyl chloride2×HCID 517096Sodium Cyanate

Product 1

HCID 76400Trichloroacetyl isocyanate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 500 ml three neck flask equipped with a reflux condenser, thermometer, 250 ml addition funnel, magnetic stirrer, and water bath was charged 43.9 grams (0.675 mole) sodium cyanate, 75 ml acetonitrile, and 125 ml toluene. To the addition funnel was added 123 grams (0.675 mole) trichloroacetyl chloride. The trichloroacetyl chloride was added under nitrogen atmosphere at a rate to maintain the reaction temperature between 30°-40° C. After the addition was complete (30 min) the water bath was replaced with an electric heating mantle and the mixture was maintained at 65°-70° C. for 1.5 hour and then cooled to room temperature with the water bath, giving a solution of trichloroacetyl isocyanate containing slurried sodium chloride.

Workup

  1. additionthermometer, 250 ml addition funnel, magnetic stirrer, and water bath
  2. temperatureto maintain the reaction temperature between 30°-40° C
  3. additionAfter the addition
  4. custom(30 min)
  5. temperaturethe mixture was maintained at 65°-70° C. for 1.5 hour

Sources & evidence

ORD record
ord-4ec8101b2dd24784acaa35252e4fc704
Source dataset
uspto-grants-1995_11
Patent number
US05468873

Reaction notes

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