Ethanol → Ethyl N-{[(3-iodophenyl)amino]carbonyl}glycinate

HRID 857104Notes

Reaction equation

HRID 857104 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[N:9]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:10]=[O:11].CCO>ClCCl>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]([NH:9][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:11])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 122713-IodoanilineHCID 76283Ethyl isocyanatoacetate

Product 1

HCID 21867094Ethyl N-{[(3-iodophenyl)amino]carbonyl}glycinate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 3-iodoaniline (9.39 g) in dichloromethane (75 ml) was treated with ethyl isocyanatoacetate (7.21 ml) at 0° C. and the mixture was stirred for 2 h and allowed to warm to 20° C. EtOH (10 ml) was added and the mixture was stirred for 15 h. The solvents were evaporated under reduced pressure and the residue was triturated in Et2O to give the title compound (12.9 g)LCMS RT=3.08 min.

Workup

  1. stirringthe mixture was stirred for 15 h
  2. customThe solvents were evaporated under reduced pressure
  3. customthe residue was triturated in Et2O

Sources & evidence

ORD record
ord-3ea316eada524378942660bec6b3bec2
Source dataset
uspto-grants-2006_12
Patent number
US07144908B2

Reaction notes

Loading…