Sodium hydride → 3-[4-chloro-2-fluoro-5-bis(methanesulfonyl)aminophenyl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 1090974Notes

Reaction equation

HRID 1090974 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][C:7]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])=[C:6]([F:28])[CH:5]=1.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>O1CCCC1>[Cl:3][C:4]1[C:9]([N:10]([S:30]([CH3:29])(=[O:32])=[O:31])[S:11]([CH3:14])(=[O:13])=[O:12])=[CH:8][C:7]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])=[C:6]([F:28])[CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 196049383-(4-chloro-2-fluoro-5-methanesulfonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Product 1

HCID 199121933-[4-chloro-2-fluoro-5-bis(methanesulfonyl)aminophenyl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 0.05g of sodium hydride(purity:60%) and 5 ml of tetrahydrofuran, 0.5g of 3-(4-chloro-2-fluoro-5-methanesulfonylaminophenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione was added at a temperature of 0° C. Then 0.11 ml of methanesulfonyl chloride was added dropwise to the resultant suspension. After stirring for 7 hburs, the reaction mixture was poured into ice water and extracted with ethyl acetate. The extract of the ethyl acetate layer was washed with a saturated sodium chloride agueous solution and dried over anhydrous sodium sulfate. Then ethyl acetate was distilled off to obtain a crude product. The obtained product was washed with diethyl ether to obtain 0.50g of the objective product as white crystals.

Workup

  1. additionwas added at a temperature of 0° C
  2. extractionextracted with ethyl acetate
  3. extractionThe extract of the ethyl acetate layer
  4. washwas washed with a saturated sodium chloride agueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen ethyl acetate was distilled off
  7. customto obtain a crude product
  8. washThe obtained product was washed with diethyl ether

Sources & evidence

ORD record
ord-5a8f3445be4b4e14840c5a3b8084ecf9
Source dataset
uspto-grants-1992_01
Patent number
US05084084

Reaction notes

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