4-Toluenesulfonyl chloride → HCID 86755465, compound

HRID 1421506Notes

Reaction equation

HRID 1421506 reaction equation
[C:1]([C:3]1[C:7]([CH:8]2[CH2:11][CH:10](O)[C:9]2([Cl:14])[Cl:13])=[CH:6][N:5]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[Cl:26])[N:4]=1)#[N:2].C(N([CH2:32][CH3:33])CC)C.[C:34]1(C)[CH:39]=C[C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(Cl)Cl>[C:1]([C:3]1[C:7]([CH:8]2[CH2:11][CH:10]([S:40]([C:37]3[C:32]([CH3:33])=[CH:39][CH:34]=[CH:35][CH:36]=3)(=[O:42])=[O:41])[C:9]2([Cl:14])[Cl:13])=[CH:6][N:5]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[Cl:26])[N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 18779839HCID 18779839, compound

Product 1

HCID 86755465HCID 86755465, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Cyano-4-(2,2-dichloro-3-hydroxycyclobutyl)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (628 mg, 1.41 mmol, Preparation 2) was dissolved in anhydrous DCM and cooled to 0° C. Triethylamine (0.27 ml, 1.98 mmol) was added dropwise followed by p-toluenesulfonyl chloride (297 mg, 1.56 mmol). The cooling bath was removed and the reaction mixture was stirred 18 hr at room temperature. The reaction mixture was poured into an equal volume of water and extracted with DCM (2×30 ml). The combined organics were washed successively with saturated sodium bicarbonate, brine then dried (Na2SO4), filtered and the solvent removed in vacuo. The residue was purified by silica chromatography (eluting with 33% DCM/hexane) to yield 131 mg of the title compound as an off-white solid.

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction mixture was poured into an equal volume of water
  3. extractionextracted with DCM (2×30 ml)
  4. washThe combined organics were washed successively with saturated sodium bicarbonate, brine
  5. dry with materialthen dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by silica chromatography (eluting with 33% DCM/hexane)

Sources & evidence

ORD record
ord-67a32f80c6104426bc9d089de1df73e7
Source dataset
uspto-grants-2000_06
Patent number
US06077859

Reaction notes

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