Ethyl 2-aminobenzoate → Ethyl 2-(2-iodophenylureido)benzoate

HRID 266672Notes

Reaction equation

HRID 266672 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=[O:10].[NH2:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:10])[NH:11][C:12]1[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 6877Ethyl 2-aminobenzoateHCID 27333851-Iodo-2-isocyanatobenzene

Product 1

HCID 10549494Ethyl 2-(2-iodophenylureido)benzoateYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-iodophenyl isocyanate (3.36 g, 13.7 mmol) in THF (250 mL) was added ethyl 2-aminobenzoate (5.1 mL, 34.5 mmol). The resulting mixture was stirred at room temperature for 8 hours, evaporated and chromatographed (silica gel, 10% EtOAc in hexanes) to give 4.4 g (78%) of ethyl 2-(2-iodophenylureido)benzoate as a white solid, mp 162°-164° C.

Workup

  1. customevaporated
  2. customchromatographed (silica gel, 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-313a4509f53a45f882ea62ba6133800b
Source dataset
uspto-grants-1997_07
Patent number
US05652237

Reaction notes

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