2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzenesulfonyl chloride → 3-(4-Chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 1862238Notes

Reaction equation

HRID 1862238 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[S:22](Cl)(=O)=O>C(O)(=O)C.[Zn]>[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:17])([F:18])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])=[CH:4][C:3]=1[SH:22]

Participants

4

Reactant 1

HCID 153345352-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzenesulfonyl chloride

Product 1

HCID 186192703-(4-Chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dioneYield 97.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

1.65 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]benzenesulfonyl chloride was dissolved in 16 ml of acetic acid, to this was added 4.4 g of zinc, then, they were reacted while heating under reflux. After completion of the reaction, the reaction solution was cooled, then, this was poured into ice water, extracted with ethyl acetate, and filtrated. The filtrate was separated, then, the organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and concentrated to obtain 1.35 g of 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenyl mercaptan.

Workup

  1. customthey were reacted
  2. temperaturewhile heating
  3. temperatureunder reflux
  4. customAfter completion of the reaction
  5. temperaturethe reaction solution was cooled
  6. extractionextracted with ethyl acetate
  7. filtrationfiltrated
  8. customThe filtrate was separated
  9. washthe organic layer was washed with saturated saline
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-a4e3156ef4284f35b3572c0c4ceae3fa
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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