2-Thiophenesulfonyl chloride → HCID 21800746, compound

HRID 1707938Notes

Reaction equation

HRID 1707938 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[S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1>[Cl:22][C:3]1[C:2]([NH:1][S:28]([C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)(=[O:30])=[O:29])=[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 855182-Thiophenesulfonyl chlorideHCID 186192573-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 21800746HCID 21800746, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 5 ml of pyridine was dissolved 0.32 g of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, and then 0.19 g of 2-thiophensulfonyl chloride was added to the solution 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 0.3 g of the desired compound as white crystal.

Workup

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

Sources & evidence

ORD record
ord-9dc09397e25248288ebffd5f3430f596
Source dataset
uspto-grants-1994_10
Patent number
US05356863

Reaction notes

Loading…