n-Methyl-p-aminophenol → HCID 13314817, compound

HRID 1446868Notes

Reaction equation

HRID 1446868 reaction equation
ClC1SC2C=CC(Cl)=CC=2N=1.[CH3:12][N:13]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:14]1[S:15][C:16]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:17]=2[N:18]=1.CNC1C=CC(O)=CC=1>O.C(#N)C>[CH3:12][N:13]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1)[C:14]1[S:15][C:16]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:17]=2[N:18]=1

Participants

4

Reactant 2

HCID 5931n-Methyl-p-aminophenolHCID 205535094-[N-methyl-N-(5-chloro-2-benzothiazolyl)amino]phenol 2,5-Dichlorobenzothiazole

Product 1

HCID 13314817HCID 13314817, compoundYield 170.2%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

4-[N-methyl-N-(5-chloro-2-benzothiazolyl)amino]phenol 2,5-Dichlorobenzothiazole (5.0 g) and 4-(N-methylamino)phenol (4.7 g) were added to a water/acetonitrile mixture (1:1) and the mixture was heated under reflux for a period of 24 hours. After cooling the solid was collected by filtration and recrystallised from water/acetonitrile to give 4-[N-methyl-N-(5-chloro-2-benzothiazolyl)amino]phenol (5.0 g) as colourless crystals, mp 238°-240° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for a period of 24 hours
  3. temperatureAfter cooling the solid
  4. filtrationwas collected by filtration
  5. customrecrystallised from water/acetonitrile

Sources & evidence

ORD record
ord-3173f3d3bd654d0a90bb8d4f33798502
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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