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

HRID 380387

반응식

HRID 380387 반응식
[Br: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]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH3:20].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-]>[Br: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]=[C:14]([F:19])[CH:15]=2)[N:10]=[C:9]1[CH:20]=[CH:34][C:32]1[N:33]=[C:29]([CH3:28])[S:30][CH:31]=1

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 27631912-Methyl-1,3-thiazole-4-carbaldehydeHCID 183629723-(2-bromo-phenyl)-6-fluoro-2-methyl-3H-quinazolin-4-one

생성물 1

HCID 545587883-(2-bromo-phenyl)-6-fluoro-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3H-quinazolin-4-one수율 52%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 962Water용매

실험 절차

Anhydrous zinc chloride (0.150 g, 1.1 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 (5 mL) was added. To this mixture was added 3-(2-bromo-phenyl)-6-fluoro-2-methyl-3H-quinazolin-4-one (0.182 g, 0.55 mmol), acetic anhydride (0.156 mL, 1.65 mmol), and 2-methythiazole-4-carboxaldehyde (0.209g, 1.65 mmol in 3 mL of dioxane). The reaction was refluxed 3 h, cooled to ambient temperature, and diluted with water. The mixture was repeatedly extracted with chloroform. The combined chloroform layer was washed with water and brine and finally dried over magnesium sulfate and concentrated to leave a dark residue. This residue was triturated with ether, filtered and dried to afford 0.116 g (52%) of 3-(2-bromo-phenyl)-6-fluoro-2-[2-(2-methyl-thiazol-4-yl)-vinyl]-3H-quinazolin-4-one as tan solid.

후처리

  1. custompurge in a round bottom flask with an open flame
  2. customto return to ambient temperature
  3. additiondioxane (5 mL) was added
  4. temperatureThe reaction was refluxed 3 h
  5. extractionThe mixture was repeatedly extracted with chloroform
  6. washThe combined chloroform layer was washed with water and brine
  7. dry with materialfinally dried over magnesium sulfate
  8. concentrationconcentrated
  9. customto leave a dark residue
  10. customThis residue was triturated with ether
  11. filtrationfiltered
  12. customdried

출처 및 근거

ORD 기록
ord-ef4d0eb12acd4489a925a46c1753664b
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06303615B1

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