4-Methylbenzaldehyde → 5-Nitro-2-p-tolylbenzo[d]thiazole

HRID 1111085Notes

Reaction equation

HRID 1111085 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[SH:11].[C:12]1([CH3:20])[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1>N1C=CC=CC=1>[CH3:20][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[S:11][C:3]3[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=3[N:1]=2)=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 77254-MethylbenzaldehydeHCID 63364002-Amino-4-nitrobenzenethiol

Product 1

HCID 221533055-Nitro-2-p-tolylbenzo[d]thiazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 153.2 g (0.9 mole) of 2-amino-4-nitrothiophenol in pyridine is added 108.1 g (0.9 mole) of 4-tolualdehyde, and the reaction is heated at 100° C. until the starting materials are consumed. After cooling to room temperature, the mixture is acidified with cold 2N HCl, and the intermediate benzthiazoline is collected by filtration. The benzthiazoline is dissolved in methanol, then ferric chloride is added, and the solution is warmed at 40° C. for about 2 hours until oxidation to the benzthiazole is complete. The product is recrystallized from ethanol.

Workup

  1. customare consumed
  2. temperatureAfter cooling to room temperature
  3. filtrationthe intermediate benzthiazoline is collected by filtration
  4. dissolutionThe benzthiazoline is dissolved in methanol
  5. additionferric chloride is added
  6. temperaturethe solution is warmed at 40° C. for about 2 hours until oxidation to the benzthiazole
  7. customThe product is recrystallized from ethanol

Sources & evidence

ORD record
ord-ef8be7f63e6b4f77b92af929e1eabe0a
Source dataset
uspto-grants-1990_12
Patent number
US04978476

Reaction notes

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