m-Chloroperbenzoic acid → HCID 23086907, compound

HRID 900831Notes

Reaction equation

HRID 900831 reaction equation
CS[C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=2[F:15])[S:5][N:4]=1.Cl[C:17]1[CH:18]=[C:19](C=CC=1)[C:20](OO)=[O:21].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[F:15][C:9]1[C:10]([F:14])=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[S:5][N:4]=[C:3]([O:21][CH2:20][C:19]#[C:18][CH3:17])[N:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 23086895HCID 23086895, compound

Product 1

HCID 23086907HCID 23086907, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Methylthio-5-(2,3-difluorophenyl)-1,2,4-thiadiazole was dissolved in 14 ml of chloroform, and 279 mg of m-chloroperoxybenzoic acid (65%<) was added thereto. The mixture was stirred for 7 hours with ice-cooling, and allowed to stand at room temperature overnight. Then, the reaction mixture was added to an aqueous sodium bicarbonate solution, and layers were separated. The organic layer was concentrated. Further, toluene was added to the residue, and the mixture was concentrated. To the resulting residue were added 2 ml of N,N-dimethylformamide and 59 mg of 2-butyne-1-ol, and 59 mg of sodium hydride (60% oily) was added thereto with ice-cooling. The mixture was stirred at the same temperature for 30 minutes, and further stirred at room temperature for 3 hours. Then, the reaction mixture was poured into an aqueous saturated sodium chloride solution, and the mixture was extracted with t-butyl methyl ether. The residue obtained by concentration of the organic layer was purified by silica gel column chromatography to obtain 95 mg of 5-(2,3-difluorophenyl)-3-(2-butynyloxy)-1,2,4-thiadiazole (the compound (16) of the present invention).

Workup

  1. temperaturecooling
  2. waitto stand at room temperature overnight
  3. customwere separated
  4. concentrationThe organic layer was concentrated
  5. additionFurther, toluene was added to the residue
  6. concentrationthe mixture was concentrated
  7. additionTo the resulting residue were added 2 ml of N,N-dimethylformamide and 59 mg of 2-butyne-1-ol, and 59 mg of sodium hydride (60% oily)
  8. additionwas added
  9. temperaturewith ice-cooling
  10. stirringThe mixture was stirred at the same temperature for 30 minutes
  11. stirringfurther stirred at room temperature for 3 hours
  12. additionThen, the reaction mixture was poured into an aqueous saturated sodium chloride solution
  13. extractionthe mixture was extracted with t-butyl methyl ether
  14. customThe residue obtained by concentration of the organic layer
  15. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-829671ebdbdf4624aca23806c641fbab
Source dataset
uspto-grants-2008_04
Patent number
US07361675B2

Reaction notes

Loading…