Droxicam → HCID 13276783, compound

HRID 1284456Notes

Reaction equation

HRID 1284456 reaction equation
COC1C=CC(P2(=S)SP(C3C=CC(OC)=CC=3)(=S)[S:10]2)=CC=1.[CH3:23][N:24]1[C:29]2[C:30](=[O:41])[N:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[C:32](=O)[O:33][C:28]=2[C:27]2[CH:42]=[CH:43][CH:44]=[CH:45][C:26]=2[S:25]1(=[O:47])=[O:46]>C1(C)C(C)=CC=CC=1>[CH3:23][N:24]1[C:29]2[C:30](=[O:41])[N:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)[C:32](=[S:10])[O:33][C:28]=2[C:27]2[CH:42]=[CH:43][CH:44]=[CH:45][C:26]=2[S:25]1(=[O:47])=[O:46]

Participants

4

Reactant 2

HCID 65679DroxicamHCID 87949Lawesson's reagent

Product 1

HCID 13276783HCID 13276783, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
140 °C

Procedure

8.1 g (0.02 mols) of 2,4-bis-(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane and 3.6 g (0.01 mol) of 5-methyl-3-(2-pyridyl)-2H,5H-1,3-oxazino[5,6-c][1,2]benzothiazine-2,4-(3H)dione-6,6-dioxide in 80 ml of xylene are maintained under reflux at 140° C. for 36 hours. The mixture is subjected to chromatography over a column containing silica gel as the stationary phase by initially eluting with xylene and then with chloroform. 1.4 g (38%) of 5-methyl-3(2-pyridyl)-2H,5H-1,3-oxazino[5,6-c][1,2]benzothiazine2(3H)thione-4-one-6,6-dioxide corresponding to the following formula are recovered from the chloroform solution: ##STR9##

Workup

  1. additioncontaining silica gel as the stationary phase
  2. washby initially eluting with xylene
  3. custom1.4 g (38%) of 5-methyl-3(2-pyridyl)-2H,5H-1,3-oxazino[5,6-c][1,2]benzothiazine2(3H)thione-4-one-6,6-dioxide corresponding to the following formula are recovered from the chloroform solution

Sources & evidence

ORD record
ord-4ae110a0483d43c0893655e3e4b2682b
Source dataset
uspto-grants-1986_01
Patent number
US04563452

Reaction notes

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