Water → 4-allyl-6-amino-7-fluoro-2H-1,4-benzoxazin-3(4H)-one

HRID 2255180ノート

反応式

HRID 2255180 の反応式
[H-].[Na+].[NH2:3][C:4]1[C:5]([F:15])=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[NH:9][C:8]=2[CH:14]=1.[CH2:16](Br)[CH:17]=[CH2:18].O>CN(C)C=O>[CH2:18]([N:9]1[C:8]2[CH:14]=[C:4]([NH2:3])[C:5]([F:15])=[CH:6][C:7]=2[O:12][CH2:11][C:10]1=[O:13])[CH:17]=[CH2:16]

参加物

6

反応物 4

HCID 962WaterHCID 7841Allyl bromideHCID 24758Sodium hydride2 回HCID 103133897-Fluoro-6-amino-2H-1,4-benzoxazin-3(4H)-one

生成物 1

HCID 150796484-allyl-6-amino-7-fluoro-2H-1,4-benzoxazin-3(4H)-one収率 90.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

While kept under N2, 2.41 g (60.4 mmol) of sodium hydride (60% dispersion in oil) was washed with 10 ml hexanes and then suspended in 20 ml anhydrous dimethylformamide. A solution of 10.0 g (54.9 mmol) of 6-amino-7-fluoro-2H-1,4-benzoxazin-3(4H)-one in 100 ml of dimethyl formamide was added to the sodium hydride slurry slowly by syringe with ice cooling and the reaction mixture was stirred at room temperature for 0.5 hr. Then there was added 7.91 g (65.9 mmol) of allyl bromide by syringe with ice bath cooling. The reaction mixture was allowed to warm to room temperature, and then poured into 100 ml of water. The resulting mixture was extracted with EtOAc (2×50 ml) and the organic layers were combined and washed with water (3×50 ml), dried over Na2SO4 and filtered. The solvent was removed in vacuo to yield 11.0 g (90% yield) of 4-allyl-6-amino- 7-fluoro-2H-1,4-benzoxazin-3(4H)-one as a brown solid.

後処理

  1. temperaturecooling
  2. temperatureto warm to room temperature
  3. extractionThe resulting mixture was extracted with EtOAc (2×50 ml)
  4. washwashed with water (3×50 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-7d6eb844ff0b48119385892d7252dd35
出典データセット
uspto-grants-1993_08
特許番号
US05238908

反応ノート

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