n-Methyl-p-aminophenol → HCID 20553512, compound

HRID 1446888Notes

Reaction equation

HRID 1446888 reaction equation
Br[C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1.[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C(=O)([O-])O.[K+]>O>[CH3:10][N:11]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)[C:2]1[S:3][C:4]([N+:7]([O-:9])=[O:8])=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 5931n-Methyl-p-aminophenolHCID 182112-Bromo-5-nitrothiazoleHCID 516893Potassium Bicarbonate

Product 1

HCID 20553512HCID 20553512, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-bromo-5-nitrothiazole (4.18 g), 4-(N-methylamino)phenol and water (50 ml) was heated under reflux for a period of 18 hours. The cooled solution was neutralised with aqueous potassium hydrogen carbonate and extracted with diethyl ether. The organic extract was dried over anhydrous magnesium sulfate and the solvent removed by distillation under reduced pressure to give 4-[N-methyl-N-(5-nitro-2-thiazolyl)amino]phenol (2.51 g) as an oil. The pmr spectrum of the compound was consistent with the assigned structure (CDCl3 ; chemical shift δ ppm): 3.55, s, 3H; 5.85, br.s, 1H; 7.15, m, 4H; 8.20, s, 1H.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 18 hours
  3. extractionextracted with diethyl ether
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customthe solvent removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1850b35a97d2476786c0724bdc7536bb
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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