Hydrazine hydrate (1:1) → 2-(Benzyloxy)acetohydrazide

HRID 1434617Notes

Reaction equation

HRID 1434617 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([O:11][CH2:12][C:13](Cl)=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C.C1COCC1>[CH2:4]([O:11][CH2:12][C:13]([NH:2][NH2:3])=[O:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 177085Benzyloxyacetyl chloride

Product 1

HCID 224803422-(Benzyloxy)acetohydrazide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hydrazine hydrate (10 ml) in ethanol (100 ml) at 0° C. was added a solution of (benzyloxy)acetyl chloride (6.4 ml) in THF (40 ml) by syringe pump over 30 minutes. The reaction mixture was allowed to warm to room temperature and stirred for 18 hours. The ethanol was removed under reduced pressure and the remaining aqueous mixture extracted with dichloromethane (3×100 ml). The combined organic extracts were washed with aqueous K2CO3 (100 ml) then brine (100 ml) and dried (MgSO4). Concentration under reduced pressure gave 2-(benzyloxy)acetohydrazide as a colourless oil that crystallized on standing (5.5 g).

Workup

  1. customThe ethanol was removed under reduced pressure
  2. extractionthe remaining aqueous mixture extracted with dichloromethane (3×100 ml)
  3. washThe combined organic extracts were washed with aqueous K2CO3 (100 ml)
  4. dry with materialbrine (100 ml) and dried (MgSO4)
  5. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-773baaf734af4ec4af1e12469b8dd033
Source dataset
uspto-grants-2009_11
Patent number
US07615555B2

Reaction notes

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