Sodium hydride → HCID 19896217, compound

HRID 1196779

Reaction equation

HRID 1196779 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[NH:8][C:7](=[O:9])[NH:6][C:5](=[O:10])[CH:4]=1.[H-].[Na+].Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][C:19]([N+:25]([O-:27])=[O:26])=[CH:18][C:17]=1[C:28]([F:31])([F:30])[F:29]>CN(C)C=O>[N+:25]([C:19]1[CH:20]=[C:21]([N+:22]([O-:24])=[O:23])[CH:16]=[C:17]([C:28]([F:29])([F:30])[F:31])[C:18]=1[N:8]1[C:3]([C:2]([F:1])([F:11])[F:12])=[CH:4][C:5](=[O:10])[NH:6][C:7]1=[O:9])([O-:27])=[O:26]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67851Benzene, 2-chloro-1,5-dinitro-3-(trifluoromethyl)-HCID 2338906-(Trifluoromethyl)uracil

Product 1

HCID 19896217HCID 19896217, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

1.0 g of 6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione was added to 10 ml of dimethylformamide, followed by addition of 0.65 g of sodium hydride (purity: 55%) with stirring at 0° C. The mixed solution was stirred at room temperature for 30 minutes, then cooled to 0° C. and added dropwise with a 5 ml dimethylformamide solution of 1.89 g of 2-chloro-3,5-dinitrobenzotrifluoride. After the solution was further stirred at room temperature for 3 hours, the solvent was distilled away under reduced pressure. After addition of cooled dilute hydrochloric acid thereto, the residue was extracted with 100 ml of ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate and then the solvent was distilled away under reduced pressure to form a crude product. This crude product was recrystallized from a mixed solvent of chloroform and petroleum ether to obtain 0.77 g of the objective compound.

Workup

  1. stirringThe mixed solution was stirred at room temperature for 30 minutes
  2. temperaturecooled to 0° C.
  3. stirringAfter the solution was further stirred at room temperature for 3 hours
  4. distillationthe solvent was distilled away under reduced pressure
  5. additionAfter addition
  6. temperatureof cooled dilute hydrochloric acid
  7. extractionthe residue was extracted with 100 ml of ethyl acetate
  8. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled away under reduced pressure
  10. customto form a crude product
  11. customThis crude product was recrystallized from a mixed solvent of chloroform and petroleum ether

Sources & evidence

ORD record
ord-c86af5ea0fd74d728bd469c85c45b158
Source dataset
uspto-grants-1992_05
Patent number
US05116404

Linked notes

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