Benzene → 3-Chloro-4-(phenethyloxy)phenyl isocyanate

HRID 848228Notes

Reaction equation

HRID 848228 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[NH2:5].[C:18](=O)([O-])[O-:19].[K+].[K+].C(Cl)(Cl)=O.C1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]=[C:18]=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 6371PhosgeneHCID 11430Potassium CarbonateHCID 16790146HCID 16790146, compound

Product 1

HCID 205666233-Chloro-4-(phenethyloxy)phenyl isocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-chloro-4-(phenethyloxy)aniline (16.06 g; 0.0648 mol), toluene (500 ml) and potassium carbonate (4.5 g; 0.035 mol) is prepared and maintained under nitrogen atmosphere. A. 12.5% solution of phosgene in benzene (65 ml; 0.072 mol) is added to the above mixture. A precipitate forms immediately. The mixture is heated at 85° C. for 45 minutes. By the end of this period the precipitate has dissolved. The reaction mixture is cooled down and filtered. The product is not isolated but rather it is used immediately.

Workup

  1. customis prepared
  2. temperaturemaintained under nitrogen atmosphere
  3. dissolutionBy the end of this period the precipitate has dissolved
  4. temperatureThe reaction mixture is cooled down
  5. filtrationfiltered
  6. customThe product is not isolated

Sources & evidence

ORD record
ord-39a0971a613f493492de9a93b3236d72
Source dataset
uspto-grants-1981_10
Patent number
US04294986

Reaction notes

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