Hydrochloric Acid → HCID 10660835, compound

HRID 1748494Notes

Reaction equation

HRID 1748494 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[O:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH2:12])=[CH:7][CH:6]=1.C(O[CH:18]=[C:19]([C:25]([CH3:27])=O)[C:20]([O:22]CC)=[O:21])C.[OH-].[Na+].Cl>C(O)C.O>[CH3:27][C:25]1[N:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][C:3]([F:13])([F:14])[F:2])=[CH:10][CH:9]=2)[N:12]=[CH:18][C:19]=1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 97734Butanoic acid, 2-(ethoxymethylene)-3-oxo-, ethyl esterHCID 27773284-(Trifluoromethoxy)phenylhydrazine hydrochloride

Product 1

HCID 10660835HCID 10660835, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
76 °C

Procedure

4-Trifluoromethoxyphenylhydrazine hydrochloride (4.0 g) and ethyl 2-ethoxymethylene-acetoacetate (3.26 g) prepared according to a method described in J. Chem. Soc. Perkin trans. I, 1875 (1988), were added to a mixed solvent of water (10 ml) and ethanol (10 ml), and stirred at 76° C. for two hours. Sodium hydroxide (1.40 g) was added to the reaction solution and the mixture was further stirred at the same temperature for an hour. Ethanol was evaporated in vacuo, hydrochloric acid (1 mole/1) was added to the aqueous solution and the precipitated solid was recrystallized from ethyl acetate to give the titled compound (3.56 g).

Workup

  1. stirringthe mixture was further stirred at the same temperature for an hour
  2. additionwas added to the aqueous solution
  3. customthe precipitated solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ab84c198e7a54e5db4b229309cbde668
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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