Tetrahydrofuran → HCID 18960431, compound

HRID 1707940Notes

Reaction equation

HRID 1707940 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[NH:22][C:23](CC(C(F)(F)F)CC(O)=O)=[O:24].S(Cl)(Cl)=O.[O:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1>>[Cl:1][C:2]1[C:3]([N:22]2[C:43](=[O:39])[CH2:42][CH:41]([C:16]([F:19])([F:18])[F:17])[CH2:40][C:23]2=[O:24])=[CH:4][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 18960420HCID 18960420, compound

Product 1

HCID 18960431HCID 18960431, compound

Procedure

To a solution of 0.50 g of 4-(N-(2-chloro-4-fluoro-5(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)phenyl)carbamoyl)-3-trifluoromethylbutyric acid and 7 ml of dry tetrahydrofuran was added dropwise 0.23 g of thionyl chloride at room temperature. After stirring for 2 hours under reflux, the temperature was cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The resulting crude product was extracted with ethyl acetate, washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain 0.50 g of the desired compound as crystal.

Workup

  1. temperatureunder reflux
  2. customthe solvent was removed by distillation under reduced pressure
  3. extractionThe resulting crude product was extracted with ethyl acetate
  4. washwashed successively with water
  5. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, and dried over anhydrous sodium sulfate
  6. customby removing ethyl acetate
  7. distillationby distillation

Sources & evidence

ORD record
ord-e58daea79f5d4e2ebf973635a9bb0447
Source dataset
uspto-grants-1994_10
Patent number
US05356863

Reaction notes

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