Water → HCID 12423504, compound

HRID 2397301Notes

Reaction equation

HRID 2397301 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH:13]=[N:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:16]=2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[OH-].[K+].S(OC)(O[CH3:32])(=O)=O.O>CN(C)C=O>[CH2:24]([O:23][C:21]([C:18]1[CH:19]=[CH:20][C:15]([N:14]([CH3:32])[CH:13]=[N:12][C:9]2[CH:8]=[CH:7][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][CH:10]=2)=[CH:16][CH:17]=1)=[O:22])[CH3:25]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 93818Benzoic acid, 4-[[[[4-(ethoxycarbonyl)phenyl]amino]methylene]amino]-, ethyl ester

Product 1

HCID 12423504HCID 12423504, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N,N'-bis(4-ethoxycarbonylphenyl)formamidine (6.8 g, 0.02 mol) in 50 ml of dimethylformamide was added 2.0 g of potassium hydroxide and 2 ml (0.02 mole) of dimethyl sulfate. The solution was stirred overnight and heated at 100° for 3 hrs. The reaction mixture was poured into 100 ml of water and the solid which precipated was collected by filtration and dried. The solid was triturated with 150 ml of benzene. The undissolved material was removed by filtration and the filtrate was concentrated to a solid residue. This solid residue was then triturated with 50 ml of chloroform. The remaining solids were removed by filtration. Concentration of the filtrate produced the desired product, mp 89°-91° C. ##STR10##

Workup

  1. temperatureheated at 100° for 3 hrs
  2. filtrationthe solid which precipated was collected by filtration
  3. customdried
  4. customThe solid was triturated with 150 ml of benzene
  5. customThe undissolved material was removed by filtration
  6. concentrationthe filtrate was concentrated to a solid residue
  7. customThis solid residue was then triturated with 50 ml of chloroform
  8. customThe remaining solids were removed by filtration

Sources & evidence

ORD record
ord-4d43ff842f9a4f7da826df13e48ea846
Source dataset
uspto-grants-1977_05
Patent number
US04021471

Reaction notes

Loading…