Potassium Carbonate → 6-Bromo-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17344

反応式

HRID 17344 の反応式
[Br:1][C:2]1[C:3](F)=[C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14].[C:18](=O)([O-])[O-:19].[K+].[K+]>O.CN(C)C=O.CO>[Br:1][C:2]1[C:3]([O:19][CH3:18])=[C:4]2[O:8][C:7]([CH:9]3[CH2:11][CH2:10]3)=[N:6][C:5]2=[C:12]([C:15]#[N:16])[C:13]=1[CH3:14]

参加物

6

反応物 2

HCID 11430Potassium Carbonate2 回HCID 510414276-Bromo-2-cyclopropyl-7-fluoro-5-methylbenzoxazole-4-carbonitrile

生成物 1

HCID 685847456-Bromo-2-cyclopropyl-7-methoxy-5-methyl-1,3-benzoxazole-4-carbonitrile収率 64%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒2 回HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
60 °C

実験手順

6-Bromo-2-cyclopropyl-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-77) (4.88 g, 16.5 mmol) was suspended in a mixed solvent of methanol (30 ml) and N,N-dimethylformamide (50 ml), potassium carbonate (4.57 g, 33.0 mmol) was added, followed by stirring at 60° C. for 30 minutes. With cooling with ice, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated away. The residue was suspended in a mixed solvent of methanol (30 ml) and N,N-dimethylformamide (50 ml), potassium carbonate (4.57 g, 33.0 mmol) was added, followed by again stirring at 60° C. for 14 hours. With cooling with ice, water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, the solvent was evaporated away. The precipitated solid was washed with a mixed solvent of ethyl acetate/isopropyl ether and collected by filtration to obtain the entitled compound (2.599 g, 64%) as a colorless solid.

後処理

  1. additionwas added
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated away
  7. additionwas added
  8. stirringby again stirring at 60° C. for 14 hours
  9. additionwas added
  10. extractionfollowed by extraction with ethyl acetate
  11. washThe organic layer was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customthe solvent was evaporated away
  14. washThe precipitated solid was washed with a mixed solvent of ethyl acetate/isopropyl ether
  15. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-4d1810d08b1f4792920fd4ab68f8ca7d
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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