Acetic Acid → HCID 53974431, compound

HRID 1166175Notes

Reaction equation

HRID 1166175 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][C:11](=O)[C:12](OCC)=O.[N:19]([O-])=O.[Na+].[CH3:23][NH:24][NH2:25].Cl.[C:27]([OH:30])(=[O:29])[CH3:28]>O.CCOCC>[CH3:23][N:24]1[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[C:10]([NH2:19])[C:11]([CH2:12][CH2:28][C:27]([OH:30])=[O:29])=[N:25]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 6061MethylhydrazineHCID 22997478Ethyl 4-(2,4-dichlorophenyl)-2,4-dioxobutanoateHCID 23668193Sodium Nitrite

Product 1

HCID 53974431HCID 53974431, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Intermediate (1) (15.4 g) was dissolved in acetic acid and sodium nitrite (3.8 g) in 15 ml water was added slowly. After the exothermic reaction was complete, and the reaction mixture began to cool, methyl hydrazine (6 ml) was added. The reaction mixture was allowed to stir overnight, or until the mixture became yellow. The mixture was concentrated to dryness, giving a yellow oil. This oil was suspended between ether and 2N HCl. The aqueous solution was separated and neutralized with sodium bicarbonate and the slightly basic solution was extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated, yielding 1-methyl-3-carboxyethyl-4-amino-5-(2,4-dicliloroplienyl)pyrazole (intermediate 2), which was used without purification in the next step.

Workup

  1. customAfter the exothermic reaction
  2. temperatureto cool
  3. concentrationThe mixture was concentrated to dryness
  4. customgiving a yellow oil
  5. customThe aqueous solution was separated
  6. extractionthe slightly basic solution was extracted with ethyl acetate
  7. dry with materialThe ethyl acetate layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-235905e7b6b846979f11ef9126c7737a
Source dataset
uspto-grants-2003_09
Patent number
US06613777B1

Reaction notes

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