Benzyl isocyanate → ethyl 2-(1-Methyl-2-(benzylcarbamoyl)hydrazinyl)acetate

HRID 576875Notes

Reaction equation

HRID 576875 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH2:3].[CH2:10]([N:17]=[C:18]=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:3][C:18](=[O:19])[NH:17][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 20288078Ethyl 2-(1-methylhydrazinyl)acetate

Product 1

HCID 66977957ethyl 2-(1-Methyl-2-(benzylcarbamoyl)hydrazinyl)acetateYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(1-methylhydrazinyl)acetate (Compound XL-1) 10 ml (76 mmol) in tetrahydrofuran 40 ml, benzyl isocyanate 11.1 g (83.3 mmol) was added at 0° C. and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate 150 ml and washed with water 75 ml and brine 75 ml. The organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to obtain the title compound 15.2 g (76%).

Workup

  1. washwashed with water 75 ml and brine 75 ml
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e456841d45a84c60b5e7cea3ed743214
Source dataset
uspto-grants-2015_05
Patent number
US09040531B2

Reaction notes

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