P-Phenylenediamine → 1-(4-Aminophenyl)-3-ethylurea

HRID 1475002Notes

Reaction equation

HRID 1475002 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[CH2:9]([N:11]=[C:12]=[O:13])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH2:9]([NH:11][C:12]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1)=[O:13])[CH3:10]

Participants

5

Reactant 3

HCID 7814P-PhenylenediamineHCID 8022Ethyl isocyanateHCID 11430Potassium Carbonate

Product 1

HCID 220610271-(4-Aminophenyl)-3-ethylureaYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,4-diaminobenzene (4 g, 37 mmol), ethyl isocyanate (1 mL, 12.6 mmol) and potassium carbonate (8.72 g, 63 mmol) in THF (20 mL) was stirred at room temperature overnight. The reaction mixture was partitioned in 1N HCl solution (80 mL) and ethyl acetate (80 mL). The aqueous layer was extracted with ethyl acetate (4×80 mL). The combined organic layers was dried, evaporated, recrystallized from MeOH/CH2Cl2/hexanes to give 4-(ethylaminocarbonylamino)aniline (1.4 g, 62%) as a beige solid.

Workup

  1. customThe reaction mixture was partitioned in 1N HCl solution (80 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (4×80 mL)
  3. customThe combined organic layers was dried
  4. customevaporated
  5. customrecrystallized from MeOH/CH2Cl2/hexanes

Sources & evidence

ORD record
ord-15c8575e93524dc29470d18708a34ca2
Source dataset
uspto-grants-2015_04
Patent number
US09018204B1

Reaction notes

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