n-Methyl-p-aminophenol → 4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenol

HRID 1446874Notes

Reaction equation

HRID 1446874 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:20]=2[N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(C(C)=O)C.O>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)[C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:20]=2[N:21]=1

Participants

7

Reactant 4

HCID 5931n-Methyl-p-aminophenolHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 103975782,5-Dichlorobenzooxazole

Product 1

HCID 133148194-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A solution of the sulfate salt of 4-(N-methylamino)phenol (0.008 mol, 2.76 g) in methyl ethyl ketone (25 ml) containing pure potassium carbonate (0.008 mol, 1.1 g) was warmed to reflux and a solution of 2,5-dichlorobenzoxazole (0.016 mol, 3.0 g) in methyl ethyl ketone (25 ml) was added dropwise over 2 hours. The resulting mixture was heated at reflux for a further hour, stood overnight, then stirred at room temperature for a further 8 hours. The solvent was then evaporated leaving a white solid. This was treated with a mixture of water (25 ml) and saturated aqueous sodium carbonate solution (25 ml). The solid was collected, washed with water, dried by suction and recrystallised three times from boiling toluene. Yield 1.4 g, mp 216°-217° C.; ir and pmr spectra and analysis consistent with assigned structure.

Workup

  1. temperaturewas warmed
  2. temperatureto reflux
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for a further hour
  5. customThe solvent was then evaporated
  6. customleaving a white solid
  7. customThe solid was collected
  8. washwashed with water
  9. customdried by suction
  10. customrecrystallised three times

Sources & evidence

ORD record
ord-361b7305a21046b298020cef63fa536d
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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