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Acetic Anhydride → HCID 53753113, compound

HRID 380386
Notes
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Reaction equation

HRID 380386 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3007855
Zincchloride
Catalyst
HCID 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, then dioxane (6 mL) was 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 4 d, 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 combined chloroform layer was washed with aqueous bisulfite, water and brine and finally dried over sodium sulfate and concentrated to leave 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
  3. additiondioxane (6 mL) was added
  4. temperatureThe reaction was refluxed 4 d
  5. extractionThe mixture was repeatedly extracted with chloroform
  6. washThe combined chloroform layer was washed with aqueous bisulfite, water and brine
  7. dry with materialfinally dried over sodium sulfate
  8. concentrationconcentrated
  9. customto leave a dark residue
  10. customThis residue was triturated with ether
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-0ed40d359fc340498d8e623c8245b08d
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06303615B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes