2-Naphthylamine → 2-naphthylurethane

HRID 1646958Notes

Reaction equation

HRID 1646958 reaction equation
[CH2:1]([O:3][C:4](Cl)=[O:5])[CH3:2].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[NH2:17].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl.O>[CH2:1]([O:3][C:4]([NH:17][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 70572-NaphthylamineHCID 10928Ethyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 6119952-naphthylurethaneYield 84%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 16.7 g of ethoxycarbonyl chloride and 20 ml of methylene chloride is added dropwise to a mixture of 20.0 g of 2-naphthylamine, 17.6 g of sodium bicarbonate, 100 ml of water and 200 ml of methylene chloride under ice-cooling and stirring. The mixture is stirred overnight at room temperature. Chloroform is added to the mixture and the organic layer is separated, dried and treated with charcol. The residue is recrystallized from ethyl acetate-hexane to give 25.26 g of N-ethoxycarbonyl-2-naphthylamine.

Workup

  1. temperaturecooling
  2. stirringThe mixture is stirred overnight at room temperature
  3. customthe organic layer is separated
  4. customdried
  5. additiontreated with charcol
  6. customThe residue is recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-70756edcf8db46189dc5d10c8b0e85b5
Source dataset
uspto-grants-1993_01
Patent number
US05182296

Reaction notes

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