Benzyl isocyanate → HCID 67304487, compound

HRID 2361940Notes

Reaction equation

HRID 2361940 reaction equation
[CH2:1]([N:4]([C:6]([CH3:13])([CH3:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH2:5])[CH:2]=[CH2:3].[CH2:14]([N:21]=[C:22]=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1.C(OCC)(=O)C>[CH2:1]([N:4]([C:6]([CH3:12])([CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:5][C:22](=[O:23])[NH:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 86658796HCID 86658796, compound

Product 1

HCID 67304487HCID 67304487, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(1-allylhydrazinyl)-2-methylpropanoate (Compound XIV-1) (4.33 g, 23.25 mmol) in THF was added benzyl isocyanate (2.87 ml, 23.25 mmol) and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (100 ml) and the mixture was washed with water (100 ml) and brine (100 ml). Then the organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The crude residue was subjected to silica gel column chromatography (eluent: n-hexane:ethylacetate=1:1 to 1:2) to obtain the title compound (2.55 g, 35%).

Workup

  1. washthe mixture was washed with water (100 ml) and brine (100 ml)
  2. dry with materialThen the organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-318481676e7743c5ac1218ac3b3ea224
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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