Acetic Anhydride → 3-(2-chloro-phenyl)-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3H-quinazolin-4-one

HRID 381272

Reaction equation

HRID 381272 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH3:19].C(OC(=O)C)(=O)C.[CH3:27][C:28]1[S:29][CH:30]=[C:31]([CH:33]=O)[N:32]=1>O.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:19]=[CH:33][C:31]1[N:32]=[C:28]([CH3:27])[S:29][CH:30]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 9567MecloqualoneHCID 27631912-Methyl-1,3-thiazole-4-carbaldehyde

Product 1

HCID 536846473-(2-chloro-phenyl)-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3H-quinazolin-4-oneYield 73.2%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

Anhydrous zinc chloride (0.136 g, 1.0 mmol) was fused with a nitrogen purge in a round bottom flask with an open flame. The reaction vessel was allowed to return to ambient temperature, at which time dioxane (10 mL) was then added. To this mixture was added 3-(2-chloro-phenyl)-2-methyl-3H-quinazolin-4-one (0.135 g, 0.50 mmol), acetic anhydride (0.141 mL, 1.5 mmol), and 2-methylthiazole-4-carboxaldehyde (0.191 g, 1.5 mmol). The reaction was refluxed for 3 hours, and was then allowed to cool to ambient temperature. Once the reaction had cooled to abient temperature it was diluted with water. The resulting mixture was repeatedly extracted with chloroform. The combined chloroform layers were washed with water and brine, dried over sodium sulfate and then concentrated to yield a waxy tan solid. This residue was triturated with ether, filtered and dried to afford 0.139 g (73%) of 3-(2-chloro-phenyl)-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3H-quinazolin-4-one as tan solid.

Workup

  1. custompurge in a round bottom flask with an open flame
  2. customto return to ambient temperature, at which time dioxane (10 mL)
  3. additionwas then added
  4. temperatureThe reaction was refluxed for 3 hours
  5. temperatureOnce the reaction had cooled
  6. extractionThe resulting mixture was repeatedly extracted with chloroform
  7. washThe combined chloroform layers were washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto yield a waxy tan solid
  11. customThis residue was triturated with ether
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-ac9b6712cc394d44a61c723c7a35aecd
Source dataset
uspto-grants-2001_10
Patent number
US06306864B1

Linked notes

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