Water → HCID 9806099, compound

HRID 1274350Notes

Reaction equation

HRID 1274350 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1[S:22][CH:23]=[CH:24][CH:25]=1.[F:26][C:27]([F:31])([F:30])[S:28]Cl.O>ClCCl>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#[N:20])[C:3]=1[C:21]1[S:22][C:23]([S:28][C:27]([F:31])([F:30])[F:26])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67900Methanesulfenyl chloride, trifluoro-HCID 9930987HCID 9930987, compound

Product 1

HCID 9806099HCID 9806099, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

To a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(thien-2-yl)pyrazole (0.806 g) in dry dichloromethane (25 ml) at room temperature was added a solution of stannic chloride (500 μl) in dry dichloromethane (5 ml). To this was added 7.2 ml of a 50 mg/ml solution of trifluoromethylsulphenyl chloride in dichloromethane and the mixture was stirred for 48 hours after which it was poured onto a mixture of ice, water and dichloromethane. The aqueous layer was separated and washed with dichloromethane. The combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution, dried and evaporated. The residue was purified by column chromatography on silica gel (40 g) eluted with dichloromethane:hexane (1:1). Combination and evaporation of suitable fractions gave the title compound as a white solid, m.p. 162-3° C.

Workup

  1. customThe aqueous layer was separated
  2. washwashed with dichloromethane
  3. washThe combined organic layers were washed with saturated aqueous sodium hydrogen carbonate solution
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (40 g)
  7. washeluted with dichloromethane:hexane (1:1)
  8. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-6ef21c67235648d59d913db2cbc7b491
Source dataset
uspto-grants-2000_12
Patent number
US06156782

Reaction notes

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