Pyridine → HCID 178510673, compound

HRID 1089886Notes

Reaction equation

HRID 1089886 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]#[N:20])[NH:14]1.N1C=CC=CC=1.[F:27][C:28]([F:32])([F:31])[S:29]Cl>ClCCl>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:10])([F:9])[F:11])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([OH:18])=[C:16]([S:29][C:28]([F:32])([F:31])[F:27])[C:15]([C:19]#[N:20])=[N:14]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67900Methanesulfenyl chloride, trifluoro-HCID 19978766HCID 19978766, compound

Product 1

HCID 178510673HCID 178510673, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.25 g (0.78 mmole) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyanopyrazol-5-one in 15 ml of dichloromethane and 0.069 ml (0.86 mmole) of pyridine, cooled to -70° C. and kept under nitrogen, was added 0.1 ml (1.0 mmole) of trifluoromethanesulfenyl chloride. After stirring for 3 hrs., the reaction was allowed to warm to ambient temperature. The excess of trifluoromethanesulfenyl chloride was removed and the reaction mixture was diluted with ethyl acetate, washed with water, dried and concentrated to an orange colored oil. Chromatographic purification afforded 0.04 g of white solid, m.p. 325° C. (decomp.).

Workup

  1. customThe excess of trifluoromethanesulfenyl chloride was removed
  2. additionthe reaction mixture was diluted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated to an orange colored oil
  6. customChromatographic purification

Sources & evidence

ORD record
ord-61f56023c57b4518a14ee48d340628d8
Source dataset
uspto-grants-1992_01
Patent number
US05079370

Reaction notes

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