Acetic Acid → HCID 14855575, compound

HRID 477388Notes

Reaction equation

HRID 477388 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[F:10][C:11]([F:23])([F:22])[C:12]1[CH:16]=[C:15]([O:17][CH2:18][C:19](O)=[O:20])[O:14][N:13]=1.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C>C1COCC1>[CH2:1]([N:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:19](=[O:20])[CH2:18][O:17][C:15]1[O:14][N:13]=[C:12]([C:11]([F:23])([F:10])[F:22])[CH:16]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7670N-EthylanilineHCID 10868DicyclohexylcarbodiimideHCID 14855464HCID 14855464, compound

Product 1

HCID 14855575HCID 14855575, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.30 ml (2.37 mmole) of N-ethylaniline and 0.50 g (2.37 mmole) of 2-(3-trifluoromethyl-5-isoxazolyloxy)acetic acid were dissolved in 2.4 ml of dry THF and to the solution was added 0.60 g (2.61 mmole) of dicyclohexylcarbodiimide. After being stirred at room temperature for one hour, the reaction mixture was allowed to stand overnight at room temperature. After the addition of glacial acetic acid (0.2 ml), the mixture was stirred at room temperature for 30 minutes and the precipitated crystals were filtered off. The filtrate was evaporated under reduced pressure and the residue was purified by chromatography on silica gel to give 638 mg of the titled compound as a pale red viscous liquid, yield 85.7%.

Workup

  1. waitto stand overnight at room temperature
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. filtrationthe precipitated crystals were filtered off
  4. customThe filtrate was evaporated under reduced pressure
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-8f4606f8f40f4bbbbb515a71ce510246
Source dataset
uspto-grants-1989_12
Patent number
US04888044

Reaction notes

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