Diphosgene → HCID 19832694, compound

HRID 2051099Notes

Reaction equation

HRID 2051099 reaction equation
[CH2:1]([N:3]([CH2:15][CH3:16])[C:4](=[O:14])[C:5]1[CH:10]=[C:9]([NH2:11])[C:8]([F:12])=[CH:7][C:6]=1[Cl:13])[CH3:2].[O:17]=[C:18](Cl)OC(Cl)(Cl)Cl>C(OCC)(=O)C>[CH2:15]([N:3]([CH2:1][CH3:2])[C:4](=[O:14])[C:5]1[CH:10]=[C:9]([N:11]=[C:18]=[O:17])[C:8]([F:12])=[CH:7][C:6]=1[Cl:13])[CH3:16]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 19832696HCID 19832696, compound

Product 1

HCID 19832694HCID 19832694, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

13.5 g of of N,N-diethyl-5-amino-2-chloro-4-fluorobenzamide in 150 ml of ethyl acetate are added dropwise while stirring within 30 minutes to a solution, heated to 70° C., of 6.7 ml of diphosgene in 50 ml of ethyl acetate. The reaction mixture is then heated at reflux temperature for 2 hours. Subsequently, the solvent is distilled off at normal pressure and the residue is distilled in a bulb-tube. There is obtained N,N-diethyl-2-chloro-4-fluoro-5-isocyanatobenzamide, b.p. 170° C./0.06 mmHg; nD 1.542, used as the starting material in Example 3.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureat reflux temperature for 2 hours
  3. distillationSubsequently, the solvent is distilled off at normal pressure
  4. distillationthe residue is distilled in a bulb-tube

Sources & evidence

ORD record
ord-7bf53490ba5d4294bf93cc7f3d512c57
Source dataset
uspto-grants-1991_05
Patent number
US05017211

Reaction notes

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