Methylhydrazine → HCID 178439467, compound

HRID 327017Notes

Reaction equation

HRID 327017 reaction equation
[C:1]([CH2:6][C:7]([O:9]CC)=O)(=O)[CH:2]([CH3:4])[CH3:3].[CH3:12][NH:13][NH2:14]>C(O)C>[OH:9][C:7]1[N:13]([CH3:12])[N:14]=[C:1]([CH:2]([CH3:4])[CH3:3])[CH:6]=1

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 81583Ethyl isobutyrylacetate

Product 1

HCID 178439467HCID 178439467, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 30.0 grams of ethyl isobutyrylacetate in 130 ml of ethanol (anhydrous,5% methanol) at 10 C. was added dropwise over 30 minutes a solution of 8.7 grams of methyl hydrazine in 30 mls of ethanol. The reaction temperature did not exceed 20 C. After twenty minutes of additional stirring the cooling bath was removed and 2 ml of glacial acetic acid was added. After one hour of stirring at room temperature the reaction was then refluxed for four hours. After stirring overnight at room temperature the reaction was concentrated to yield a yellowish solid. This solid was stirred with 100 ml of hexanes for 30 minutes and the off-white solid was collected and rinsed with 75 ml of hexanes. The solid was dried in a vacuum oven at 45 C. overnight to yield 23.3 g of the desired product, mp 120-122 C.

Workup

  1. customwas removed
  2. addition2 ml of glacial acetic acid was added
  3. stirringAfter one hour of stirring at room temperature the reaction
  4. temperaturewas then refluxed for four hours
  5. stirringAfter stirring overnight at room temperature the reaction
  6. concentrationwas concentrated
  7. customto yield a yellowish solid
  8. customthe off-white solid was collected
  9. washrinsed with 75 ml of hexanes
  10. customThe solid was dried in a vacuum oven at 45 C

Sources & evidence

ORD record
ord-741e2202c8184a9e9dd3d2829348c1fc
Source dataset
uspto-grants-1993_12
Patent number
US05272128

Reaction notes

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