Potassium Carbonate → 4-[(2-Methoxycarbonyl-2-methylpropionyloxy)-methoxy]-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide

HRID 1583304Notes

Reaction equation

HRID 1583304 reaction equation
[CH3:1][N:2]1[S:11](=[O:13])(=[O:12])[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]([OH:14])=[C:3]1[C:15]([NH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][N:23]=1)=[O:16].C(=O)([O-])[O-].[K+].[K+].[CH3:30][C:31]([CH3:41])([C:37]([O:39][CH3:40])=[O:38])[C:32]([O:34][CH2:35]I)=[O:33].[K+].[Br-]>CC(C)=O>[CH3:40][O:39][C:37]([C:31]([CH3:41])([CH3:30])[C:32]([O:34][CH2:35][O:14][C:4]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[S:11](=[O:13])(=[O:12])[N:2]([CH3:1])[C:3]=1[C:15]([NH:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][N:23]=1)=[O:16])=[O:33])=[O:38]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 253877Potassium BromideHCID 20260333Iodomethyl methyl 2,2-dimethylmalonateHCID 54676228Piroxicam

Product 1

HCID 135066664-[(2-Methoxycarbonyl-2-methylpropionyloxy)-methoxy]-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a dry round bottomed flask equipped with a reflux condenser and stirring bar were added piroxicam (1.50 g, 4.53 mmol), potassium carbonate (1.24 g, 8.98 mmol), iodomethyl methyl 2,2-dimethylmalonate (1.48 g, 5.17 mmol) and dry acetone (15 mL). The heterogenous reaction mixture was heated to reflux under a nitrogen atmosphere for 3 hours. Chromatographed title product was isolated according to the method of Example 5, 0.95 g (43.2%) light yellow solid which was recrystallized from toluene-hexane to give light yellow crystals: mp 112°-114° C.; IR (KBr) 1690, 1680 cm-1 ; 1H NMR (CDCl3) delta 1.28 (s, 6H), 3.11 (s, 3H), 3.62 (s, 3H), 5.76 (s, 2H), 7.08-7.18 (m, 1H), 7.70-7.88 (m, 4H), 7.89-7.99 (dd, J=8 Hz, J=4 Hz, 1H), 7.30-7.44 (m, 2H), 9.42 (s, 1H); precise mass calcd for C22H23N3O6S m/e 489.1205, found 489.1230.

Workup

  1. customTo a dry round bottomed flask equipped with a reflux condenser
  2. temperatureThe heterogenous reaction mixture was heated
  3. temperatureto reflux under a nitrogen atmosphere for 3 hours
  4. customChromatographed title product
  5. customwas isolated
  6. customwas recrystallized from toluene-hexane
  7. customto give light yellow crystals

Sources & evidence

ORD record
ord-c1a8b0897e5643e2be329978fd9528ce
Source dataset
uspto-grants-1985_11
Patent number
US04551452

Reaction notes

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