Carbamic acid, ethyl ester → Fluquazone

HRID 1395147Notes

Reaction equation

HRID 1395147 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][NH:4][C:5]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[C:22](=O)([O:24]CC)[NH2:23]>C(Cl)(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]([F:21])([F:20])[CH2:3][N:4]1[C:5]2[C:6](=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:23][C:22]1=[O:24]

Participants

5

Reactant 2

HCID 5641Carbamic acid, ethyl esterHCID 898212-(2,2,2-Trifluoroethylamino)-5-chlorobenzophenone

Product 1

HCID 219069FluquazoneYield 73.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 62.7 g of 2-(2,2,2-trifluoroethylamino)-5-chlorobenzophenone, 107 g of ethyl carbamate and 10 g of zinc chloride was heated at 190° C. (oil bath temperature) for 3 hours. After cooling, the reaction mixture was dissolved in chloroform and the insoluble material was filtered off. The chloroform solution was washed successively with dilute hydrochloric acid and water, and dried over anhydrous sodium sulfate. Then the solvent was removed under reduced pressure and the residual solid was washed 3 times with 100 ml of isopropyl ether and dried to give 49.5 g of 1-(2,2,2-trifluoroethyl)-4-phenyl-6-chloro-2(1H)-quinazolinone as a pale gray powder. Recrystallization from ethanol gave pale yellow needles, m.p. 186.5°-187.5° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe insoluble material was filtered off
  3. washThe chloroform solution was washed successively with dilute hydrochloric acid and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThen the solvent was removed under reduced pressure
  6. washthe residual solid was washed 3 times with 100 ml of isopropyl ether
  7. customdried

Sources & evidence

ORD record
ord-2104eabaa0df4b47b01079133fcb8174
Source dataset
uspto-grants-1980_05
Patent number
US04202895

Reaction notes

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