Triethylamine → 2-Chloro-1-ethoxy-4-isocyanatobenzene

HRID 882921Notes

Reaction equation

HRID 882921 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[Cl:18])[CH3:9].Cl[C:20](Cl)([O:22]C(=O)OC(Cl)(Cl)Cl)Cl>CCOC(C)=O>[CH2:8]([O:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:20]=[O:22])=[CH:13][C:12]=1[Cl:18])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 127487363-Chloro-4-ethoxyaniline

Product 1

HCID 30159672-Chloro-1-ethoxy-4-isocyanatobenzene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-Ethoxy-2-chloro-4-isocyanato-benzene is prepared by addition of triethylamine to a solution of 4-ethoxy-3-chlorophenylamine in EtOAc at 0-5° C. Triphosgene is added and the reaction mixture is slowly heated to reflux over 2 h. The solvent is removed in vacuo and the crude product is filtered through silica to afford the title compound.

Workup

  1. temperaturethe reaction mixture is slowly heated
  2. temperatureto reflux over 2 h
  3. customThe solvent is removed in vacuo
  4. filtrationthe crude product is filtered through silica

Sources & evidence

ORD record
ord-ae35c798b7ed4080a800857f520a5976
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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