2-Naphthylamine → 2-naphthylurethane

HRID 1729319Notes

Reaction equation

HRID 1729319 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-95b3a56ca5cf4691b932be2e8b04a40d
Source dataset
uspto-grants-1994_07
Patent number
US05332754

Reaction notes

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