Ethyl isocyanate → HCID 21712326, compound

HRID 366162Notes

Reaction equation

HRID 366162 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:17]([N:19]=[C:20]=[O:21])[CH3:18]>C(O)C>[CH2:10]([N:9]([C:20]([NH:19][CH2:17][CH3:18])=[O:21])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 10656659TERT-BUTYL 2-BENZYLHYDRAZINECARBOXYLATE

Product 1

HCID 21712326HCID 21712326, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N'-benzylhydrazinecarboxylic acid tert-butyl ester (2.5 g, 11.8 mmol) in 99% ethanol (40 ml) was added ethyl isocyanate (1.1 g, 15.2 mmol) and the mixture was stirred for 2 h. Then the mixture was concentrated in vacuo and chromatographed on silica (20 g) with petrol ether/ethyl acetate 3:2 to give 3.0 g of 2-benzyl-1-tert-butoxycarbonyl-4-ethylsemicarbazide.

Workup

  1. concentrationThen the mixture was concentrated in vacuo
  2. customchromatographed on silica (20 g) with petrol ether/ethyl acetate 3:2

Sources & evidence

ORD record
ord-85acc104d7f642ba91e1696dbe5b675b
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

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