2-Amino-4-methylpyridine → 2-(4-Methylpyridin-2-yl)-3-oxo-3h-benzo[d]isothiazole

HRID 367234

Reaction equation

HRID 367234 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.Cl[S:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14]>N1C=CC=CC=1>[CH3:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([N:1]2[C:13](=[O:14])[C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:10]2)[CH:7]=1

Participants

4

Reactant 2

HCID 15332-Amino-4-methylpyridineHCID 109107152-(Chlorothio)-benzoyl chloride

Product 1

HCID 158713272-(4-Methylpyridin-2-yl)-3-oxo-3h-benzo[d]isothiazoleYield 37.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

Using the method of Fischer and Hurni (Arzneimittel Forsch., 1964;14:1301) 5.4 g (0.05 mol) of 2-amino-4-methylpyridine in 50 mL of pyridine at 10° C. was reacted with 10.3 g (0.05 mol) of 2-chlorosulfanylbenzoyl chloride. The mixture was heated to 50° C. and maintained at that temperature for 2 hours. The mixture was cooled to 25° C. and filtered. The solid was recrystallized from benzene to give 4.5 g of the title compound, mp 195-196.5° C.

Workup

  1. customat 10° C.
  2. temperaturemaintained at that temperature for 2 hours
  3. temperatureThe mixture was cooled to 25° C.
  4. filtrationfiltered
  5. customThe solid was recrystallized from benzene

Sources & evidence

ORD record
ord-ae0aa4274a964f7e97fc87c298c1df3c
Source dataset
uspto-grants-2000_10
Patent number
US06133270

Linked notes

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