Triethylamine → HCID 67121104, compound

HRID 1510434Notes

Reaction equation

HRID 1510434 reaction equation
C(N(CC)CC)C.[F:8][C:9]([F:22])([F:21])[C:10]1[CH:20]=[CH:19][C:13]([C:14]([CH2:16][C:17]#[N:18])=[O:15])=[CH:12][CH:11]=1.Cl[C:24](=[N:30]O)[C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(O)C>[C:17]([C:16]1[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:30][O:15][C:14]=1[C:13]1[CH:19]=[CH:20][C:10]([C:9]([F:21])([F:22])[F:8])=[CH:11][CH:12]=1)#[N:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6816376Ethyl chloro(hydroximino)acetateHCID 105605263-Oxo-3-[4-(trifluoromethyl)phenyl]propanenitrile

Product 1

HCID 67121104HCID 67121104, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Triethylamine (0.98 mL, 7.0 mmol) was added to a −5° C. solution of 4-trifluoromethylbenzoylacetonitrile (1.5 g, 7.0 mmol) in ethanol (15 mL) and the mixture was stirred for 20 minutes. A solution of ethyl 2-chloro-2-(hydroxyimino)acetate (1.06 g, 7.0 mmol) in ethanol (5 mL) was added to the reaction over 15 minutes. After stirring at room temperature for 72 hours, the cream-colored solid which formed was collected by filtration, washed with cold water and dried in vacuo to obtain ethyl 4-cyano-5-(4-(trifluoromethyl)phenyl)isoxazole-3-carboxylate (1.84 g, 5.93 mmol).

Workup

  1. stirringAfter stirring at room temperature for 72 hours
  2. customthe cream-colored solid which formed
  3. filtrationwas collected by filtration
  4. washwashed with cold water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-6208102ac77b4a8da062db77ac2b8c3d
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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