Ethanol → Ethyl 2-{[(3-iodophenyl)amino]carbonyl}hydrazinecarboxylate

HRID 857133Notes

Reaction equation

HRID 857133 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[NH:2][NH2:3].[I:8][C:9]1[CH:10]=[C:11]([N:15]=[C:16]=[O:17])[CH:12]=[CH:13][CH:14]=1.C(O)C>ClCCl>[I:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]([NH:3][NH:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 44990001-Iodo-3-isocyanatobenzene

Product 1

HCID 21867116Ethyl 2-{[(3-iodophenyl)amino]carbonyl}hydrazinecarboxylateYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of ethyl carbazate (1.25 g) in dichloromethane (20 ml) was treated with 3-iodophenylisocyanate (1.7 g) at 0° C. The reaction mixture was allowed to warm to 20° C. and stirred for 2 h. Ethanol (2 ml) was added and the mixture was stirred for 0.5 h. The solvents were removed under reduced pressure and the residue was triturated in diethyl ether. The white solid was collected by filtration to give the title compound (2.4 g). LCMS RT=2.81 min

Workup

  1. stirringthe mixture was stirred for 0.5 h
  2. customThe solvents were removed under reduced pressure
  3. customthe residue was triturated in diethyl ether
  4. filtrationThe white solid was collected by filtration

Sources & evidence

ORD record
ord-e603dd6d9b484b44a170870b3bcfc6ce
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

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