Acetic Anhydride → 6-fluoro-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3-(2-methyl-phenyl)-3H-quinazolin-4-one

HRID 381268

反応式

HRID 381268 の反応式
[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[CH3:19])[C:5]2=[O:20].C(OC(=O)C)(=O)C.[CH3:28][C:29]1[S:30][CH:31]=[C:32]([CH:34]=O)[N:33]=1>O.[Cl-].[Zn+2].[Cl-]>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]=[CH:34][C:32]1[N:33]=[C:29]([CH3:28])[S:30][CH:31]=1)[N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])[C:5]2=[O:20]

参加物

6

反応物 3

HCID 7918Acetic AnhydrideHCID 634674(3H)-Quinazolinone, 6-fluoro-2-methyl-3-(2-methylphenyl)-HCID 27631912-Methyl-1,3-thiazole-4-carbaldehyde

生成物 1

HCID 544906406-fluoro-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3-(2-methyl-phenyl)-3H-quinazolin-4-one収率 21.2%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 962Water溶媒

実験手順

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, then dioxane (10 mL) was added. To this mixture was added 6-fluoro-2-methyl-3-(2-methyl-phenyl)-3H-quinazolin-4-one (0.1 34 g, 0.5 mmol), acetic anhydride (0.141 mL, 1.5 mmol), and 2-methylthiazole-4-carboxaldehyde (0.191 g, 1.5 mmol). The reaction was refluxed 3.5 hours, at which time the reaction was allowed to cool to ambient temperature. Once the reaction had cooled to ambient temperature it was diluted with water. The resulting mixture was repeatedly extracted with chloroform. The chloroform extracts were combined and the resulting chloroform layer was washed with water and brine, dried over sodium sulfate and concentrated to leave a dark residue. This residue was triturated with ether, filtered and dried to afford 0.04 g (21%) of 6-fluoro-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3-(2-methyl-phenyl)-3H-quinazolin-4-one as a tan solid.

後処理

  1. custompurge in a round bottom flask with an open flame
  2. customto return to ambient temperature
  3. additiondioxane (10 mL) was added
  4. temperatureThe reaction was refluxed 3.5 hours, at which time the reaction
  5. temperatureOnce the reaction had cooled to ambient temperature it
  6. extractionThe resulting mixture was repeatedly extracted with chloroform
  7. washthe resulting chloroform layer was washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto leave a dark residue
  11. customThis residue was triturated with ether
  12. filtrationfiltered
  13. customdried

出典と根拠

ORDレコード
ord-74e20885c0254ba7bb0aa49c5dd1e4fd
出典データセット
uspto-grants-2001_10
特許番号
US06306864B1

関連ノート

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