Trichloroacetyl chloride → HCID 12812383, compound

HRID 328128Notes

Reaction equation

HRID 328128 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[NH:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[C:10]([NH:12][CH2:13][C:14]([F:17])([F:16])[F:15])=[O:11])([O-:3])=[O:2].[H-].[Na+].ClC(Cl)(Cl)[C:29](Cl)=[O:30]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[C:8]3[C:9](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:10](=[O:11])[N:12]([CH2:13][C:14]([F:15])([F:16])[F:17])[C:29]2=[O:30])[CH:22]=[CH:23][CH:24]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 24758Sodium hydrideHCID 54499784HCID 54499784, compound

Product 1

HCID 12812383HCID 12812383, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.4 g of 2-(m-nitroanilino)-N-(2,2,2-trifluoroethyl) benzamide and 25 ml of dry tetrahydrofuran was added 0.5 g of approximately 55 % sodium hydride, and stirring was continued for one hour at room temperature. To this was added dropwise under cooling 5.5 g of trichloroacetyl chloride and the mixture was allowed to stand for one hour at room temperature, and then refluxed for 5 hours. After the reaction was complete, the solvent was distilled off from the resulting mixture under reduced pressure. To the residue was added water to precipitate a crude product. This product was recrystallized from ethanol to give 3.2 g of 1-(m-nitrophenyl)-3-(2,2,2-trifluoroethyl) quinazoline-2,4(1H, 3H)-dione as pale yellow prisms, melting at 182°-184° C.

Workup

  1. additionTo this was added dropwise
  2. waitto stand for one hour at room temperature
  3. temperaturerefluxed for 5 hours
  4. distillationthe solvent was distilled off from the resulting mixture under reduced pressure
  5. additionTo the residue was added water
  6. customto precipitate a crude product
  7. customThis product was recrystallized from ethanol

Sources & evidence

ORD record
ord-aa87fe4a9f66434db50fc492bf330b89
Source dataset
uspto-grants-1977_04
Patent number
US04016166

Reaction notes

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