Benzocaine → N,N-Diphenyl-N'-(4-ethoxycarbonylphenyl)formamidine

HRID 2397302

Reaction equation

HRID 2397302 reaction equation
[C:1]1([N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:22][C:23]1[CH:33]=[CH:32][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:24]=1.[OH-].[NH4+]>C(Cl)(Cl)Cl.O>[C:1]1([N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[N:22][C:23]2[CH:24]=[CH:25][C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:32][CH:33]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 2337BenzocaineHCID 14923Ammonium HydroxideHCID 24819Phosphorus pentachlorideHCID 69081Diphenylformamide

Product 1

HCID 20038066N,N-Diphenyl-N'-(4-ethoxycarbonylphenyl)formamidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a solution of N,N-diphenylformamide (19.7 g, 0.10 mol) in 100 ml of chloroform was added 22.8 g (0.11 mol) of phosphorus pentachloride in small portions. After the addition was completed the solution was refluxed for 1 hr. Ethyl 4-aminobenzoate (16.5 g, 0.10 mol) was added in small portions and the solution was refluxed 1 hr. The solution was poured into 100 ml of water and neutralized with concentrated ammonium hydroxide. The chloroform phase was separated, dried (MgSO4), filtered and concentrated to yield a yellow oil. Purification by chromatography using silica gel/benzene yielded the desired product. ##STR11##

Workup

  1. additionAfter the addition
  2. temperaturewas refluxed for 1 hr
  3. temperaturethe solution was refluxed 1 hr
  4. customThe chloroform phase was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a yellow oil
  9. customPurification by chromatography

Sources & evidence

ORD record
ord-f50c3fba6a594a7aaff9f89d302785d6
Source dataset
uspto-grants-1977_05
Patent number
US04021471

Linked notes

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