Acetic Anhydride → HCID 53753113, compound

HRID 381270Notes

Reaction equation

HRID 381270 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[F:19])[C:5]2=[O:20].C(OC(=O)C)(=O)C.[CH3:28][N:29]([CH2:31][C:32]1[S:33][CH:34]=[C:35]([CH:37]=O)[N:36]=1)[CH3:30].C(=O)([O-])[O-].[Na+].[Na+]>O.[Cl-].[Zn+2].[Cl-]>[CH3:28][N:29]([CH2:31][C:32]1[S:33][CH:34]=[C:35]([CH:37]=[CH:12][C:7]2[N:6]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[F:19])[C:5](=[O:20])[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=3)[N:8]=2)[N:36]=1)[CH3:30]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 632424(3H)-Quinazolinone, 6-fluoro-3-(2-fluorophenyl)-2-methyl-HCID 226116842-[(Dimethylamino)methyl]-1,3-thiazole-4-carbaldehyde

Product 1

HCID 53753113HCID 53753113, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

Anhydrous zinc chloride (0.106 g, 0.78 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 (6 mL) was then added. To this mixture was added 6-fluoro-3-(2-fluoro-phenyl)-2-methyl-3H-quinazolin-4-one (0.108 g, 0.39 mmol), acetic anhydride (0.111 mL, 1.18 mmol), and 2-dimethylaminomethylthiazole-4-carboxaldehyde (0.280 g, 1.18 mmol in 4 mL of dioxane). The reaction was refluxed for four days, at which time it was cooled to ambient temperature, and diluted with water. Sodium carbonate was added until the mixture was basic. The mixture was repeatedly extracted with chloroform. The chloroform extracts were combined to form a chloroform layer which was washed with aqueous bisulfite, water and brine and finally was dried over sodium sulfate and concentrated to yield a dark residue. This residue was triturated with ether. filtered and dried to afford 0.051 g (31%) of 2-[2-(2-dimethylaminomethyl-thiazol-4-yl)-vinyl]-6-fluoro-3-(2-fluoro-phenyl)-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 (6 mL)
  3. additionwas then added
  4. temperatureThe reaction was refluxed for four days, at which time it
  5. extractionThe mixture was repeatedly extracted with chloroform
  6. customto form a chloroform layer which
  7. washwas washed with aqueous bisulfite, water and brine
  8. dry with materialfinally was dried over sodium sulfate
  9. concentrationconcentrated
  10. customto yield a dark residue
  11. customThis residue was triturated with ether
  12. filtrationfiltered
  13. customdried

Sources & evidence

ORD record
ord-ec78658da9584af198856fa90abaf8b0
Source dataset
uspto-grants-2001_10
Patent number
US06306864B1

Reaction notes

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