Pyridine → HCID 178499159, compound

HRID 1089884Notes

Reaction equation

HRID 1089884 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([O:21][CH3:22])=[O:20])[NH:14]1.ClCCl.N1C=CC=CC=1.[F:32][C:33]([F:37])([F:36])[S:34]Cl>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([OH:18])=[C:16]([S:34][C:33]([F:37])([F:36])[F:32])[C:15]([C:19]([O:21][CH3:22])=[O:20])=[N:14]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 67900Methanesulfenyl chloride, trifluoro-HCID 2741096HCID 2741096, compound

Product 1

HCID 178499159HCID 178499159, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 10 g (0.028 mol) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(methoxycarbonyl)-pyrazol-5-one in 150 ml of dichloromethane containing 2.45 g (0.03 mole) of pyridine, cooled to -10° to 0° C., was added 3.75 ml (0.04 mole) of trifluoromethanesulfenyl chloride. The reaction mixture was allowed to stir overnight, then diluted with ethyl acetate and washed with water. The organic layer was dried and concentrated to afford 13.0 g of a tan colored solid. Recrystallization from hexane:methyl-t-butyl ether afforded 5.5 g of a product, m.p. 216.5°-217.5° C.

Workup

  1. washwashed with water
  2. customThe organic layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2406867fe1104dba9a98cfc9a7261312
Source dataset
uspto-grants-1992_01
Patent number
US05079370

Reaction notes

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