4-Aminobenzonitrile → HCID 15521688, compound

HRID 351629Notes

Reaction equation

HRID 351629 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]=[C:8]=[O:9])=[O:5])[CH3:2].[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:5])[CH2:6][NH:7][C:8]([NH:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=1)=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 133964-AminobenzonitrileHCID 76283Ethyl isocyanatoacetate2×

Product 1

HCID 15521688HCID 15521688, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethoxycarbonylmethyl isocyanate (24.5 ml, 0.212 mol) in DMF (100 ml) a solution of 4-aminobenzonitrile (25 g, 0.212 mol) in DMF (100 ml) was added within 30 min at 0° C. Stirring was continued for 7 d and additional ethoxycarbonylmethyl isocyanate was added periodically (18.5 ml, 0.156 mol). The solvent was removed in vacuo and the residue was stirred in ethyl acetate/diethyl ether. The mixture was filtered to give the title compound (39.12 g, 74%; white solid of m.p. 140-144° C.) which was used without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. stirringthe residue was stirred in ethyl acetate/diethyl ether
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-f4ffec44ee2c4957886144be6e954d9f
Source dataset
uspto-grants-2004_06
Patent number
US06743790B2

Reaction notes

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