Nitrogen → 2-Chloro-2-phenylacetonitrile

HRID 276142

Reaction equation

HRID 276142 reaction equation
C(Cl)([Cl:3])=O.[CH:5]1[CH:10]=[CH:9][C:8]([CH:11](O)[C:12]#[N:13])=[CH:7][CH:6]=1.N#N>C1(C)C=CC=CC=1>[Cl:3][CH:11]([C:8]1[CH:9]=[CH:10][CH:5]=[CH:6][CH:7]=1)[C:12]#[N:13]

Participants

5

Reactant 3

HCID 947NitrogenHCID 6371Phosgene3×HCID 10758Mandelonitrile

Product 1

HCID 123763172-Chloro-2-phenylacetonitrileYield 967.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

150 g of toluene and 7 g (0.02 mol) of Cyanex® 923 are initially introduced into a phosgenation apparatus with attached carbonic acid condenser and heated. At 99° C., 13 g of phosgene are gassed in over the course of 10 minutes. Thereafter, over the course of 2 hours, 192 g (1.44 mol) of benzaldehyde cyanohydrin and a further 149 g (total=172 g or 1.74 mol) of phosgene are added in parallel. The internal temperature is maintained between 99 and 102° C. throughout. After a post-reaction of 60 minutes at 99° C., excess phosgene is stripped out using N2 at 50° C. for 2.5 h. The discharge of 359 g is fractionally distilled on a 30 cm Vigreux column. The main fraction passes over at 0.6 mbar and a head temperature of from 68 to 73° C. 192.7 g (88.3% of theory) of α-chlorophenylacetonitrile are isolated.

Workup

  1. temperatureheated
  2. customAt 99° C.
  3. customare gassed in over the course of 10 minutes
  4. temperatureThe internal temperature is maintained between 99 and 102° C. throughout
  5. customAfter a post-reaction of 60 minutes at 99° C.
  6. customat 50° C.
  7. customfor 2.5 h
  8. distillationThe discharge of 359 g is fractionally distilled on a 30 cm Vigreux column
  9. customof from 68 to 73° C

Sources & evidence

ORD record
ord-e7f51422316643b2bba09bd562315cb9
Source dataset
uspto-grants-2002_03
Patent number
US06353127B1

Linked notes

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