Benzyl isocyanate → Ethyl 2-(1-allyl-2-(benzylcarbamoyl)hydrazinyl)acetate

HRID 718880Notes

Reaction equation

HRID 718880 reaction equation
[CH2:1]([N:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH2:5])[CH:2]=[CH2:3].[CH2:12]([N:19]=[C:20]=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:4]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:5][C:20](=[O:21])[NH:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 45082254Ethyl (1-allylhydrazino)acetate

Product 1

HCID 59541461Ethyl 2-(1-allyl-2-(benzylcarbamoyl)hydrazinyl)acetateYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of ethyl 2-(1-allylhydrazinyl)acetate (Compound XV-1) 6.9 g (44 mmol) in tetrahydrofuran 40 ml, benzyl isocyanate 6.1 g (46 mmol) was added at 0° C. and at room temperature for 3.5 hours. 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 with magnesium sulfate and filtered. The filtrate was concentrated in vacuo to obtain the title compound 9.43 g (75%).

Workup

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

Sources & evidence

ORD record
ord-07efee049aa44daeb5f0b224566d5de1
Source dataset
uspto-grants-2015_11
Patent number
US09193734B2

Reaction notes

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