Sodium Iodide → 4-[1-(Octanoyloxy)ethoxy]-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide

HRID 1583303Notes

Reaction equation

HRID 1583303 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+].[C:30]([O:39][CH:40](Cl)[CH3:41])(=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].[I-].[Na+]>C1(C)C=CC=CC=1.CCCCCC.CC(C)=O>[C:30]([O:39][CH:40]([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])[CH3:41])(=[O:38])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 202603341-Chloroethyl octanoateHCID 54676228Piroxicam

Product 1

HCID 135066544-[1-(Octanoyloxy)ethoxy]-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21889329Toluene hexaneSolvent

Procedure

To a round bottomed flask equipped with a reflux condenser and stirring bar were added piroxicam (3.00 g, 9.1 mmol), potassium carbonate (2.50 g, 18.1 mmol), alpha-chloroethyl octanoate (5.6 g, 27.0 mmol) and acetone (45 mL). The heterogenous reaction mixture was heated to reflux under a nitrogen atmosphere. After one hour sodium iodide (4.52 g, 30.2 mmol) was added and reflux continued an additional 72 hours. Chromatographed title product was isolated according to Example 5 as a white foam which oiled from toluene/hexane, but crystallized from the oil upon refrigeration. Collected were 2.19 g white crystals from two crops (4.4 mmol, 48.2%); mp 90°-91° C.; IR (KBr) 1766, 1675 cm-1 ; 1H NMR (CDCl3) delta 0.85 (t, J=7 Hz, 3H), 1.02-1.34 (m, 8H), 1.45 (d, br quintet, 2H), 1.73 (d, J=6 Hz, 3H), 2.08-2.33 (m, 2H), 3.12 (s, 3H), 6.40 (q, J=6 Hz, 1H), 7.06-7.17 (m, 1H), 7.63-7.95 (m, 5H), 8.30-8.42 (m, 2H), 9.56 (br s, 1H): precise mass calcd for C23H27N3O5S m/e (P+ --C2H4O) 457.1429, found 457.1700.

Workup

  1. customTo a round bottomed flask equipped with a reflux condenser
  2. temperatureThe heterogenous reaction mixture was heated
  3. temperatureto reflux under a nitrogen atmosphere
  4. temperaturereflux
  5. customChromatographed title product
  6. customwas isolated
  7. customcrystallized from the oil upon refrigeration
  8. customCollected

Sources & evidence

ORD record
ord-0d4d33f04e5c43c49451f70724d905cc
Source dataset
uspto-grants-1985_11
Patent number
US04551452

Reaction notes

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