Methanesulfenyl chloride, trifluoro- → HCID 18329013, compound

HRID 1249837Notes

Reaction equation

HRID 1249837 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]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[CH:16][C:15]([C:26]#[N:27])=[N:14]1.[F:28][C:29]([F:33])([F:32])[S:30]Cl>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[C:16]([S:30][C:29]([F:33])([F:32])[F:28])[C:15]([C:26]#[N:27])=[N:14]1

Participants

4

Reactant 2

HCID 67900Methanesulfenyl chloride, trifluoro-HCID 18329015HCID 18329015, compound

Product 1

HCID 18329013HCID 18329013, compoundYield 64.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 10 ml of dichloromethane was suspended 0.5 g of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-(4-pyridylmethylamino)pyrazole obtained in Example 1 above, and 0.2 g of trifluoromethylsulfenyl chloride in 10 ml of dichloromethane was added thereto dropwise at −20° C. The mixture was taken out of the cooling bath. After stirring for 3 hours, ice-water was added to the mixture to extract. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography to yield 0.4 g of compound No. 1 shown in Table 1 below. The NMR data of the compound were as follows.

Workup

  1. customdropwise at −20° C
  2. extractionto extract
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5ea473b42a71456eab7b0e0a0c8188e2
Source dataset
uspto-grants-2002_01
Patent number
US06335357B1

Reaction notes

Loading…