Acetic Acid → HCID 57470283, compound

HRID 1672989Notes

Reaction equation

HRID 1672989 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[C:5](=O)[CH2:6][C:7](=O)[CH3:8])[CH3:2].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:14]=1[NH:20][NH2:21].C(O)(=O)C>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([CH3:8])[N:20]([C:14]2[C:13]([Cl:12])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:19])[N:21]=1)=[O:11])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 69208Ethyl 2,4-dioxovalerateHCID 84634(2,6-Dichlorophenyl)hydrazine

Product 1

HCID 57470283HCID 57470283, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Into a 2000 mL flask was weighed 35.33 g (223.5 mmol) of 2,4-dioxopentanoic acid ethyl ester, 50 g (234.7 mmol) of 2,6 dichlorophenyl hydrazine, 400 mL of acetic acid and 400 mL of ethanol. The resulting solution was heated at 80° C. for 18 h and was then cooled and was washed into a separatory funnel with 1.0 M aq. NaOH and ethyl acetate. The organic layer was separated, washed with sat. aq. NaHCO3, brine, dried over Na2SO4, and was concentrated in vacuo. The residue was recrystallized from EtOH-heptanes to afford 1-(2,6-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylic acid ethyl ester (44.6 g, 60%); 1H NMR (400 MHz, DMSO-d6): δ 7.67 (d J=7.67 Hz, 2H), 7.57 (m, 1H), 4.17 (q, J=7.07 Hz 2H), 1.97 (s, 3H); 1.18 (t, J=7.07 Hz 3H), MS (ES): 321 [M+Na]+.

Workup

  1. customInto a 2000 mL flask was weighed
  2. temperaturewas then cooled
  3. washwas washed into a separatory funnel with 1.0 M aq. NaOH and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with sat. aq. NaHCO3, brine
  6. dry with materialdried over Na2SO4
  7. concentrationwas concentrated in vacuo
  8. customThe residue was recrystallized from EtOH-heptanes

Sources & evidence

ORD record
ord-d006647832bb4ee887a27e8c7e0dc12e
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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