2-Thiophenecarbonyl chloride → HCID 18960416, compound

HRID 1707943Notes

Reaction equation

HRID 1707943 reaction equation
[NH2:1][C:2]1[C:3]([Cl:22])=[CH:4][C:5]([F:21])=[C:6]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])[CH:7]=1.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28](Cl)=[O:29]>N1C=CC=CC=1>[Cl:22][C:3]1[C:2]([NH:1][C:28](=[O:29])[C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)=[CH:7][C:6]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[C:5]([F:21])[CH:4]=1

Participants

4

Reactant 2

HCID 789282-Thiophenecarbonyl chlorideHCID 186192573-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 18960416HCID 18960416, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 5 ml of pyridine was dissolved 0.34 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and 0.17 g of 2-thiophencarbonyl chloride was added thereto at 5° C. or lower. Thereafter, the temperature was increased to room temperature and the reaction was continued overnight. Then, pyridine was removed by distillation and the residue was dissolved in ethyl acetate. The solution was washed successively with water, diluted hydrochloric acid and a saturated saline solution, and dried over anhydrous sodium sulfate followed by removing ethyl acetate by distillation to obtain a crude product. This was washed with diisopropyl ether to obtain 0.30 g of the desired compound as white crystal.

Workup

  1. additionwas added
  2. customat 5° C.
  3. customThen, pyridine was removed by distillation
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washThe solution was washed successively with water, diluted hydrochloric acid
  6. dry with materiala saturated saline solution, and dried over anhydrous sodium sulfate
  7. customby removing ethyl acetate
  8. distillationby distillation
  9. customto obtain a crude product
  10. washThis was washed with diisopropyl ether

Sources & evidence

ORD record
ord-cb2cf5d0197c419bb9766374b6961aec
Source dataset
uspto-grants-1994_10
Patent number
US05356863

Reaction notes

Loading…