2-Aminopyridine → 7-Chloro-3-(pyrid-2-yl)amino-4H-1,2,4-benzothiadiazine 1,1-dioxide

HRID 1066169Notes

Reaction equation

HRID 1066169 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][C:7](S(C)=O)=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1>ClC1C=C(C)C=CC=1>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]2[NH:6][C:7]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[N:8][S:9](=[O:11])(=[O:10])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 211979037-Chloro-3-methylsulfinyl-4H-1,2,4-benzothiadiazine 1,1-dioxide

Product 1

HCID 111096297-Chloro-3-(pyrid-2-yl)amino-4H-1,2,4-benzothiadiazine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 79313-ChlorotolueneSolvent

Procedure

7-Chloro-3-methylsulfinyl-4H-1,2,4-benzothiadiazine 1,1-dioxide (0.25 g) and 2-aminopyridine (0.25 g) in 3-chlorotoluene (5 mL) was heated at 150° C. for 1 h. After cooling, the white precipitate was collected by filtration and washed with diethylether. The insoluble material was dissolved in 1M NaOH (20 mL), treated with charcoal, filtered, and the filtrate was adjusted to pH 3 with 6N HCl. The precipitate was collected by filtration, washed with water, dissolved in hot DMF (15 mL), mixed with an equal volume of distilled water and cooled. The white precipitate was collected by filtration, washed with water and dried (yield: 0.12 g); m.p. >310° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe white precipitate was collected by filtration
  3. washwashed with diethylether
  4. dissolutionThe insoluble material was dissolved in 1M NaOH (20 mL)
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with water
  9. dissolutiondissolved in hot DMF (15 mL)
  10. additionmixed with an equal volume of distilled water
  11. temperaturecooled
  12. filtrationThe white precipitate was collected by filtration
  13. washwashed with water
  14. customdried (yield: 0.12 g)

Sources & evidence

ORD record
ord-92da720591f6476c88608fb152406d38
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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