Ethyl chloroformate → HCID 11421894, compound

HRID 1360979Notes

Reaction equation

HRID 1360979 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.Cl[C:35]([O:37][CH2:38][CH3:39])=[O:36].[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:35]([O:37][CH2:38][CH3:39])=[O:36])=[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 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86611439HCID 86611439, compound

Product 1

HCID 11421894HCID 11421894, compoundYield 84%

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 stirred under an atmosphere of nitrogen for 2 hours at 20° C. Ethyl chloroformate (0.029 g, 0.3 mmol) was 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 give the title compound as a white powder (0.098 g, Compound 6, yield: 81%), 19F-NMR: −63.8, −78.6.

Workup

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

Sources & evidence

ORD record
ord-5f57ec2158ce4dab8784be44730ee54e
Source dataset
uspto-grants-2011_02
Patent number
US07879897B2

Reaction notes

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