Pyridine → HCID 178499159, compound

HRID 728339Notes

Reaction equation

HRID 728339 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 mole) 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-afd7e8caeaa740279fc45a75f3746ec7
Source dataset
uspto-grants-1991_09
Patent number
US05047550

Reaction notes

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