2-Aminopyridine → HCID 54717104, compound

HRID 1448588Notes

Reaction equation

HRID 1448588 reaction equation
[C:1]([C:5]1[N:6]([CH3:18])[S:7](=[O:17])(=[O:16])[C:8]2[C:9](=[CH:12][S:13][C:14]=2[Cl:15])[C:10]=1[OH:11])([O:3]C)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1>CC1C=CC=CC=1C>[Cl:15][C:14]1[S:13][CH:12]=[C:9]2[C:8]=1[S:7](=[O:17])(=[O:16])[N:6]([CH3:18])[C:5]([C:1](=[O:3])[NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)=[C:10]2[OH:11]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 54717101HCID 54717101, compound

Product 1

HCID 54717104HCID 54717104, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2.2 g. of 3-carbomethoxy-7-chloro-4-hydroxy-2-methyl-2H-thieno-[3,4-e]-1,2-thiazine-1,1-dioxide, 0.9 g. of 2-aminopyridine and 240 ml. of absolute o-xylene is boiled under reflux for 7 hours while stirring, approximately 80 ml. of the o-xylene being slowly distilled during the first 2 hours. After the reaction mixture has been cooled to room temperature, it is concentrated to approximately 60 ml. by evaporation in vacuo and cooled in an ice bath. The product that crystallizes out is suction filtered, washed with ether, dried and recrystallized from acetonitrile, and 7-chloro-4-hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2H-thieno[3,4-e]-1,2-thiazine-1,1-dioxide having a melting point of 218°-220° (with decomposition) is obtained.

Workup

  1. additionA mixture of 2.2 g
  2. temperatureunder reflux for 7 hours
  3. distillationof the o-xylene being slowly distilled during the first 2 hours
  4. concentrationit is concentrated to approximately 60 ml
  5. customby evaporation in vacuo
  6. temperaturecooled in an ice bath
  7. customThe product that crystallizes out is suction
  8. filtrationfiltered
  9. washwashed with ether
  10. customdried
  11. customrecrystallized from acetonitrile, and 7-chloro-4-hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2H-thieno[3,4-e]-1,2-thiazine-1,1-dioxide having a melting point of 218°-220° (with decomposition)
  12. customis obtained

Sources & evidence

ORD record
ord-ee0e02271bc7428e89be125b21e300aa
Source dataset
uspto-grants-1979_12
Patent number
US04180662

Reaction notes

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