Phenyl isocyanate → N-(2-Aminoethyl)-N'-phenylurea

HRID 2308972Notes

Reaction equation

HRID 2308972 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][NH2:7])(=[O:3])C.[C:8]1([N:14]=C=O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)Cl>[C:8]1([NH:14][C:1]([NH:4][CH2:5][CH2:6][NH2:7])=[O:3])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 66082N-(2-aminoethyl)acetamide

Product 1

HCID 12681829N-(2-Aminoethyl)-N'-phenylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring suspension of 0.057 mole of acetylethylene diamine in 100 ml of methylene chloride at 10° C. was added dropwise 0.057 mole of phenyl isocyanate. Soon after the addition a solid precipitated. 100 ml of anhydrous ether was added to the reaction mixture and stirring was continued for another 30 minutes. The solid was recovered by filtration, dissolved in 50 ml of 15% hydrochloric acid, and the solution was heated to 80° C. for 4 hours. Removal of the aqueous acid afforded the product which had a melting point of 190.4° C.

Workup

  1. additionSoon after the addition a solid
  2. customprecipitated
  3. addition100 ml of anhydrous ether was added to the reaction mixture
  4. filtrationThe solid was recovered by filtration
  5. dissolutiondissolved in 50 ml of 15% hydrochloric acid
  6. customRemoval of the aqueous acid
  7. customafforded the product which

Sources & evidence

ORD record
ord-86a16948fe9f4a3c9bcc7449d8956d1a
Source dataset
uspto-grants-1987_09
Patent number
US04692446

Reaction notes

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