4-Toluenesulfonyl chloride → HCID 11342821, compound

HRID 1360977Notes

Reaction equation

HRID 1360977 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]([N:18]([CH2:20][CH2:21][OH:22])[CH3:19])=[C:16]([S:23]([C:26]([F:29])([F:28])[F:27])(=[O:25])=[O:24])[C:15]([C:30]#[N:31])=[N:14]1.[H-].[Na+].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[Cl:12][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:13]1[C:17]([N:18]([CH3:19])[CH2:20][CH2:21][O:22][S:40]([C:37]2[CH:38]=[CH:39][C:34]([CH3:44])=[CH:35][CH:36]=2)(=[O:42])=[O:41])=[C:16]([S:23]([C:26]([F:29])([F:27])[F:28])(=[O:24])=[O:25])[C:15]([C:30]#[N:31])=[N:14]1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86611439HCID 86611439, compound

Product 1

HCID 11342821HCID 11342821, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(2,6-dichloro-4-trifluoromethylphenyl)-3-cyano-5-[N-(2-hydroxyethyl)-N-methylamino]-4-trifluoromethylsulfonylpyrazole (0.100 g, 0.2 mmol) and sodium hydride (0.016 g, 0.4 mmol) in dry tetrahydrofuran was stirred vigorously under an atmosphere of nitrogen for 1 hour at 20° C. 4-Toluenesulfonyl chloride (0.056 g, 0.3 mmol) was then added and stirring continued for 1 hour at 20° C. The mixture was then added to saturated ammonium chloride solution and ethyl acetate; and the organic layer washed with water and brine, dried (sodium sulfate) and evaporated. The residue was purified by flash column chromatography eluting with heptane/ethyl acetate (4:1) to afford the title compound as a fine white powder (0.074 g, Compound 93, yield 55%), 19F-NMR: −64.2, −79.2.

Workup

  1. washand the organic layer washed with water and brine
  2. dry with materialdried (sodium sulfate)
  3. customevaporated
  4. customThe residue was purified by flash column chromatography
  5. washeluting with heptane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-591efb6a25554be3b208e3273105a195
Source dataset
uspto-grants-2011_02
Patent number
US07879897B2

Reaction notes

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