Methylhydrazine → Benzyl 1-methylhydrazinecarboxylate

HRID 1196229Notes

Reaction equation

HRID 1196229 reaction equation
[CH3:1][NH:2][NH2:3].C(N(CC)CC)C.[CH2:11]([O:18][C:19](Cl)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O1CCCC1>[C:12]1([CH2:11][O:18][C:19]([N:2]([CH3:1])[NH2:3])=[O:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 11217590Benzyl 1-methylhydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold, stirred solution of 36.8 (0.8 mol; 42.49 ml) methylhydrazine and 161.6 g (1.6 mol, 224 ml) triethylamine in 700 ml tetrahydrofuran were added dropwise 136.5 g (0.8 mol, 113.6 ml) benzylchloroformate. After stirring at room temperature overnight, the tetrahydrofuran was evaporated and the residue was worked up with ethylacetate/water (pH=9.0. Insoluble material was removed by filtration and the organic phase was washed (H2O), dried (MgSO4) and evaporated. The oily residue was stirred with 1 1. of ether, the etherial solution was decanted from insoluble material and evaporated to give 61 g of an oil which was dissolved in 200 ml MeOH containing 25 ml conc. HCl. After evaporation to dryness, the residue was recrystallized from EtOH/ ethylacetate to give 22.0 g of the hydrochloride of 2 as colorless crystals. This material was dissolved in water and the pH was adjusted to 9.0. Extraction with ethylacetate, drying of the organic phase (MgSO4) and evaporation yielded 19.0 g of the title compound as a colorless oil.

Workup

  1. customthe tetrahydrofuran was evaporated
  2. customInsoluble material was removed by filtration
  3. washthe organic phase was washed (H2O)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. stirringThe oily residue was stirred with 1 1
  7. customof ether, the etherial solution was decanted from insoluble material
  8. customevaporated

Sources & evidence

ORD record
ord-9709276f30e845538d79ebe88aff8d7b
Source dataset
uspto-grants-1992_05
Patent number
US05112968

Reaction notes

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