2-Aminopyridine → 3,4-Dihydro-2-methyl-3-oxo-4-(2-pyridyl-carbamoyl)-2H-thieno [2,3-e] 1,2-thiazine 1,1-dioxide

HRID 46732Notes

Reaction equation

HRID 46732 reaction equation
CO[C:3]([CH:5]1[C:10]2[S:11][CH:12]=[CH:13][C:9]=2[S:8](=[O:15])(=[O:14])[N:7]([CH3:16])[C:6]1=[O:17])=[O:4].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>C1(C)C(C)=CC=CC=1>[CH3:16][N:7]1[C:6](=[O:17])[CH:5]([C:3](=[O:4])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:10]2[S:11][CH:12]=[CH:13][C:9]=2[S:8]1(=[O:14])=[O:15]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 166399353,4-dihydro-4-methoxycarbonyl-2-methyl-3-oxo-2H-thieno[2,3-e] 1,2-thiazine 1,1-dioxide

Product 1

HCID 166399423,4-Dihydro-2-methyl-3-oxo-4-(2-pyridyl-carbamoyl)-2H-thieno [2,3-e] 1,2-thiazine 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

0.3 G. of 3,4-dihydro-4-methoxycarbonyl-2-methyl-3-oxo-2H-thieno[2,3-e]1,2-thiazine 1,1-dioxide and 0.13 g. of 2-aminopyridine are dissolved in 30 ml. of absolute xylene and the solution is heated for 1 hour under reflux. After cooling, the crystals are removed by filtration and recrystallized from glacial acetic acid. 3,4-Dihydro-2-methyl-3-oxo-4-(2-pyridyl-carbamoyl)-2H-thieno[2,3-e]1,2-thiazine 1,1-dioxide, melting point 255° C. to 256° C. (decomposition), is obtained.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. customthe crystals are removed by filtration
  4. customrecrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-7984c680bb364f6499e5c6804d5e09ab
Source dataset
uspto-grants-1979_11
Patent number
US04175085

Reaction notes

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