Sodium hydride → HCID 11262472, compound

HRID 1360978Notes

Reaction equation

HRID 1360978 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([Cl:14])[C:5]=1[N:15]1[C:19]([N:20]([CH2:22][CH2:23][OH:24])[CH3:21])=[C:18]([S:25]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])[C:17]([C:32]#[N:33])=[N:16]1.[F:34][C:35]([F:46])([F:45])[C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[Cl:14][C:6]1[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=[C:4]([Cl:3])[C:5]=1[N:15]1[C:19]([N:20]([CH3:21])[CH2:22][CH2:23][O:24][C:40](=[O:41])[C:39]2[CH:43]=[CH:44][C:36]([C:35]([F:34])([F:45])[F:46])=[CH:37][CH:38]=2)=[C:18]([S:25]([C:28]([F:31])([F:29])[F:30])(=[O:26])=[O:27])[C:17]([C:32]#[N:33])=[N:16]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 86611439HCID 86611439, compound

Product 1

HCID 11262472HCID 11262472, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydride (0.012 g, 0.3 mmol) was added to 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) in dry tetrahydrofuran, and the mixture vigorously stirred under a nitrogen atmosphere for 1 hour at 20° C. 4-Trifluoromethylbenzoyl chloride (0.053 g, 0.3 mmol) was added and the resulting mixture stirred for 2 hours at 20° C. The mixture was poured into 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 give the title compound as a pale oil (0.085 g, Compound 54, yield 61%), 19F-NMR: −63.7, −63.8, −78.6.

Workup

  1. stirringthe resulting mixture stirred for 2 hours at 20° C
  2. washthe organic layer washed with water and brine
  3. dry with materialdried (sodium sulfate)
  4. customevaporated
  5. customThe residue was purified by flash column chromatography
  6. washeluting with heptane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-5d1c76ec78ad4a7baae06113670ced33
Source dataset
uspto-grants-2011_02
Patent number
US07879897B2

Reaction notes

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