Phosgene → 4-(2-Naphthyloxy)phenyl isocyanate

HRID 434613Notes

Reaction equation

HRID 434613 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.[C:19](Cl)(Cl)=[O:20]>C1(C)C=CC=CC=1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][C:12]1[CH:18]=[CH:17][C:15]([N:16]=[C:19]=[O:20])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 35808292-(4-Aminophenoxy)naphthalene

Product 1

HCID 127740664-(2-Naphthyloxy)phenyl isocyanateYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 4-(2-naphthyloxy)aniline (4 g) in toluene (100 ml) was dropwise added to a solution of phosgene (3.5 g) in toluene (50 ml), and the resulting mixture was refluxed for 1 hour. After removal of the solvent from the reaction mixture by distillation under reduced pressure, the residue was distilled in vacuo to give 4-(2-naphthyloxy)phenyl isocyanate (4.1 g) as a fraction boiling at 137° to 149° C./0.8 mmHg. M.P., 75°-77° C.

Workup

  1. temperaturethe resulting mixture was refluxed for 1 hour
  2. customAfter removal of the solvent from the reaction mixture
  3. distillationby distillation under reduced pressure
  4. distillationthe residue was distilled in vacuo

Sources & evidence

ORD record
ord-0a4f79bff973439684ea4b498f9893dc
Source dataset
uspto-grants-1983_08
Patent number
US04399072

Reaction notes

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