Diphosgene → HCID 13711524, compound

HRID 1278543Notes

Reaction equation

HRID 1278543 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:5][C:3]=1[NH2:4].[O:14]=[C:15](Cl)OC(Cl)(Cl)Cl>C1COCC1.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:5][C:3]=1[N:4]=[C:15]=[O:14]

Participants

5

Reactant 2

HCID 10426DiphosgeneHCID 10536163Methyl 5-amino-2-chloro-4-fluorobenzoate

Product 1

HCID 13711524HCID 13711524, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-fluoro-4-chloro-5-methoxycarbonylaniline (1.0 g, 5 mmol) in THF (10 mL) was added dropwist to a solution of diphosgene (2.0 g, 10 mmol) in toluene (20 mL) with stirring at room temperature. The reaction mixture was stirred at room temperature for one hour and then heated to reflux for 4 hours. The mixture was then cooled to room temperature and the solvents were evaporated under reduced pressure to give 1.1 g of 2-fluoro-4-chloro-5-methoxycarbonylphenyl isocyanate as a solid. This was used for the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for one hour
  2. temperatureheated
  3. temperatureto reflux for 4 hours
  4. temperatureThe mixture was then cooled to room temperature
  5. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-0fbb8ea3211e486a94fd03207182a651
Source dataset
uspto-grants-2002_09
Patent number
US06444615B1

Reaction notes

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