Phosgene → 3-Chloro-2-(4-isocyanatophenoxy)-5-(trifluoromethyl)pyridine

HRID 637988Notes

Reaction equation

HRID 637988 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][C:5]([O:6][C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][N:8]=2)=[CH:4][CH:3]=1.[C:20](Cl)(Cl)=[O:21]>C1(C)C=CC=CC=1>[Cl:13][C:12]1[C:7]([O:6][C:5]2[CH:18]=[CH:19][C:2]([N:1]=[C:20]=[O:21])=[CH:3][CH:4]=2)=[N:8][CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 27641164-{[3-Chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}aniline

Product 1

HCID 202550553-Chloro-2-(4-isocyanatophenoxy)-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(4-aminophenoxy)-3-chloro-5-trifluoromethylpyridine (0.45 g) and a solution of phosgene in toluene (50 ml of a 12% solution) was heated at the reflux temperature for 6 hours. Evaporation of the volatile portion under reduced pressure yielded 3-chloro-5-trifluoromethyl-2-(4-isocyanatophenoxy)pyridine as a residual pale brown oil (0.5 g) which was used without further purification.

Workup

  1. customEvaporation of the volatile portion under reduced pressure

Sources & evidence

ORD record
ord-1f7da5d18cf24a83822fcd34b22e0001
Source dataset
uspto-grants-1985_12
Patent number
US04559353

Reaction notes

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