Ethyl Acetoacetate → HCID 178472852, compound

HRID 1031164Notes

Reaction equation

HRID 1031164 reaction equation
[N:1]([O-])=O.[Na+].[Cl:5][C:6]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:7]=1[NH2:8].[C:18]([O:24][CH2:25][CH3:26])(=[O:23])[CH2:19][C:20]([CH3:22])=[O:21].C([O-])(=O)C.[Na+]>S(=O)(=O)(O)O.C(O)(=O)C.C(O)C>[Cl:5][C:6]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Cl:17])[C:7]=1[NH:8][N:1]=[C:19]([C:20](=[O:21])[CH3:22])[C:18]([O:24][CH2:25][CH3:26])=[O:23]

Participants

8

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1410944-Amino-3,5-dichlorobenzotrifluorideHCID 517045Sodium AcetateHCID 23668193Sodium Nitrite

Product 1

HCID 178472852HCID 178472852, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of sodium nitrite (45 g) in concentrated sulphuric acid (340 ml) was added to a solution of 2,6-dichloro-4-trifluoromethylaniline (140 g) in glacial acetic acid (550 ml) while maintaining the temperature below 25°. The mixture was stirred at room temperature for one hour, and was added quite rapidly to a stirred mixture of ethyl acetoacetate (80 g), sodium acetate (180 g), ethanol (300 ml) and ice-water (3 1). After 1 hour, the brown solid was filtered and dried to give ethyl 2-(2,6-dichloro-4-trifluoromethylphenylhydrazono)-3-oxobutyrate.

Workup

  1. temperaturewhile maintaining the temperature below 25°
  2. waitAfter 1 hour
  3. filtrationthe brown solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-2849f3a448b64fee93e30357f17a5d7b
Source dataset
uspto-grants-1992_04
Patent number
US05109012

Reaction notes

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