Ethyl isocyanate → 4-Ethyl-1-(2-nitrobenzoyl)semicarbazide

HRID 1688093Notes

Reaction equation

HRID 1688093 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([NH:8][NH2:9])=[O:7])([O-:3])=[O:2].[N:14]([CH2:17][CH3:18])=[C:15]=[O:16]>CN(C=O)C>[CH2:17]([NH:14][C:15](=[O:16])[NH:9][NH:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][CH:12]=[CH:13][C:4]=1[N+:1]([O-:3])=[O:2])[CH3:18]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 3781218o-Nitrobenzohydrazide

Product 1

HCID 472526074-Ethyl-1-(2-nitrobenzoyl)semicarbazideYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-nitro-benzoic acid hydrazide (3 g) in DMF (20 mL) was added isocyanato-ethane (1.3 g). The reaction mixture was stirred at room temperature for 3 hours and concentrated in vacuo to provide 4 g of 4-ethyl-1-(2-nitrobenzoyl)-semicarbazide: 1H NMR (300 MHz, CDCl3) δ 8.2 (dd, 1H), 7.8 (s, 3H), 6.4 (bs, 1H), 3.3 (q, 2H), 1.2 (t, 3H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-983b627a4bf44da993ff21c191af33ac
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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