Acetone → HCID 13506647, compound

HRID 1583293Notes

Reaction equation

HRID 1583293 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+].Br[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:33](=[O:34])[O:32]1.CC(C)=O>C1(C)C=CC=CC=1.C(Cl)Cl.O>[C:33]1([C:35]2[C:40](=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:31]([O:14][C:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[S:11](=[O:13])(=[O:12])[N:2]([CH3:1])[C:3]=2[C:15]([NH:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][N:23]=2)=[O:16])[O:32]1)=[O:34]

Participants

8

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 54676228Piroxicam

Product 1

HCID 13506647HCID 13506647, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask equipped with a reflux condenser and a stirring bar were added piroxicam (3.00 g, 9.1 mmol), potassium carbonate (2.50 g, 18.2 mmol), 3-bromophthalide (prepared according to U.K. Pat. No. 1,364,672; 2.51 g, 11.8 mmol) and acetone (45 mL). The heterogenous reaction mixture was heated to reflux under a nitrogen atmosphere. After 0.5 hour the solvent was removed in vacuo leaving a brown residue which was treated with water (200 mL) and methylene chloride (200 mL). The organic layer was separated and the aqueous layer extracted with additional methylene chloride (200 mL). The combined organic extracts were washed with water (200 mL), brine (200 mL), dried (Na2SO4) and concentrated in vacuo to a brown oil. Column chromatography on silica (1:9 ethyl acetate:methylene chloride) afforded a white foam which, when dissolved in hot toluene, precipitated within a few seconds as pure white crystals: 3.42 g (7.38 mmol, 81.5%); mp 151°-152° C.; IR (KBr) 1785, 1688 cm-1 ; 1H NMR (CDCl3) delta 3.13 (s, 3H), 6.97 (s, 1H), 7.07-7.35 (m, 1H), 7.58-8.18 (m, 9H), 8.30-8.44 (m, 2H), 9.18 (br s, 1H): precise mass calcd for C23H17N3O6S m/e 463.0855, found 463.0871.

Workup

  1. customTo a round bottomed flask equipped with a reflux condenser and a stirring bar
  2. customprepared
  3. temperatureThe heterogenous reaction mixture was heated
  4. temperatureto reflux under a nitrogen atmosphere
  5. customAfter 0.5 hour the solvent was removed in vacuo
  6. customleaving a brown residue which
  7. customThe organic layer was separated
  8. extractionthe aqueous layer extracted with additional methylene chloride (200 mL)
  9. washThe combined organic extracts were washed with water (200 mL), brine (200 mL)
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo to a brown oil
  12. customColumn chromatography on silica (1:9 ethyl acetate:methylene chloride) afforded a white foam which, when
  13. customprecipitated within a few seconds as pure white crystals

Sources & evidence

ORD record
ord-7b29d0b5d4c74825b5f7c5f29bc80235
Source dataset
uspto-grants-1985_11
Patent number
US04551452

Reaction notes

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