Phosgene → 4-Phenoxymethylphenyl isocyanate

HRID 443337Notes

Reaction equation

HRID 443337 reaction equation
[O:1]([CH2:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](Cl)(Cl)=[O:17]>C1(C)C=CC=CC=1>[O:1]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([N:13]=[C:16]=[O:17])=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 127125614-(Phenoxymethyl)aniline

Product 1

HCID 234663554-Phenoxymethylphenyl isocyanateYield 61.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4-phenoxymethylaniline (10 g) in toluene (100 ml) was added dropwise to a solution of phosgene (20 g) in toluene (100 ml) at 10° to 20° C. The mixture was gradually heated and refluxed for 30 minutes. Thereafter, the reaction mixture was cooled to room temperature, and the solvent was evaporated under reduced pressure to give 7 g of 4-phenoxymethylphenyl isocyanate. M.P., 56°-57° C.

Workup

  1. temperatureThe mixture was gradually heated
  2. temperaturerefluxed for 30 minutes
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-da0c9f60cbed4183b69f066eeb8090d5
Source dataset
uspto-grants-1981_04
Patent number
US04260411

Reaction notes

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