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

HRID 1254478Notes

Reaction equation

HRID 1254478 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-f59565c1a97f488ea910b7b603e45449
Source dataset
uspto-grants-2013_06
Patent number
US08455488B2

Reaction notes

Loading…