Methylhydrazine → HCID 66958773, compound

HRID 1984444Notes

Reaction equation

HRID 1984444 reaction equation
CC(C)([O-])C.[Na+].O=[C:8]([CH:10]=[C:11]([CH3:13])[CH3:12])[CH3:9].[C:14](OCC)(=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].[CH3:24][NH:25][NH2:26]>C(O)C.C(O)(=O)C>[CH3:24][N:25]1[C:8]([CH:10]=[C:11]([CH3:13])[CH3:12])=[CH:9][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:26]1

Participants

7

Reactant 4

HCID 6061MethylhydrazineHCID 7268Diethyl OxalateHCID 8858Mesityl oxideHCID 23676156Sodium t-butoxide

Product 1

HCID 66958773HCID 66958773, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×

Procedure

Under a nitrogen atmosphere, sodium tert-butoxide (54.1 g, 0.564 mol) and ethanol (187 mL) were combined at 0° C. The mixture was stirred at ambient temperature for 30 minutes. A mixture of mesityl oxide (30 mL, 0.26 mol) and diethyl oxalate (35.6 mL, 0.26 mol) in ethanol (40 mL) was added over a period of 1 minute. The reaction mixture was stirred for 2.5 hours at ambient temperature and then cooled to 0° C. Acetic acid (131 mL) and methyl hydrazine (15.3 mL, 0.288 mol) were added. The reaction was allowed to warm to ambient temperature with stirring overnight and then concentrated under reduced pressure. The residue was diluted with chloroform (500 mL) and water (1 L) and the mixture was adjusted to pH 11 with the addition of 50% sodium hydroxide. The aqueous layer was extracted with chloroform (3×250 mL); the combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide ethyl 1-methyl-5-(2-methylprop-1-enyl)-1H-pyrazole-3-carboxylate as a black oil that was used without purification.

Workup

  1. customwere combined at 0° C
  2. additionwas added over a period of 1 minute
  3. stirringThe reaction mixture was stirred for 2.5 hours at ambient temperature
  4. temperaturecooled to 0° C
  5. temperatureto warm to ambient temperature
  6. stirringwith stirring overnight
  7. concentrationconcentrated under reduced pressure
  8. additionThe residue was diluted with chloroform (500 mL) and water (1 L)
  9. additionthe mixture was adjusted to pH 11 with the addition of 50% sodium hydroxide
  10. extractionThe aqueous layer was extracted with chloroform (3×250 mL)
  11. dry with materialthe combined organics were dried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9bbb45a294874e2b91db3898e67b0f45
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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