Hydrochloric Acid → (7,8-Difluoro-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)-oxoacetaldehyde oxime

HRID 729423

反応式

HRID 729423 の反応式
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.[OH2:8].O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[F:25][C:26]1[CH:36]=[CH:35][C:29]2[NH:30][CH:31]([CH3:34])[CH2:32][O:33][C:28]=2[C:27]=1[F:37].Cl.Cl.[NH2:40]O>O.C(O)C>[F:25][C:26]1[CH:36]=[CH:35][C:29]2[N:30]([C:3](=[O:5])[CH:2]=[N:40][OH:8])[CH:31]([CH3:34])[CH2:32][O:33][C:28]=2[C:27]=1[F:37]

参加物

8

反応物 5

HCID 313Hydrochloric Acid2 回HCID 2707Chloral HydrateHCID 62649Sodium sulfate decahydrateHCID 443297Hydroxyamine hydrochlorideHCID 102197187,8-Difluoro-2,3-dihydro-3-methyl-4H-(1,4)benzoxazine

生成物 1

HCID 73857481(7,8-Difluoro-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)-oxoacetaldehyde oxime

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

反応条件

温度
77.5 °C

実験手順

A solution of 8.27 g (50 mmol) of chloral hydrate in 125 mL of water is treated with 112.8 g (0.35 mmol) of sodium sulfate decahydrate. The mixture is stirred and treated with a solution of 7,8-difluoro-3-methyl-3,4-dihydro-2H-benz[1,4]oxazine (Chem. Pharm. Bull., 1984; 32:4907) hydrochloride prepared by dissolving 8.26 g (44.6 mmol) of the free base in 50 mmol of concentrated hydrochloric acid in 70 mL of 50% aqueous ethanol). The reaction is stirred and a solution of 9.8 g (140 mmol) of hydroxylamine hydrochloride in 50 mL of water is added. After heating at 75 to 80° C. for 3 hours, the reaction is stirred at room temperature overnight. The resulting precipitate is removed by filtration, washed with water, and the wet filter cake is dissolved in dichloromethane. The organic solution is washed with water, dried (MgSO4), decolorized with charcoal, filtered and concentrated in vacuo to give 10.5 g of the title compound, mp 188-190° C.

後処理

  1. customprepared
  2. stirringThe reaction is stirred
  3. stirringthe reaction is stirred at room temperature overnight
  4. customThe resulting precipitate is removed by filtration
  5. washwashed with water
  6. dissolutionthe wet filter cake is dissolved in dichloromethane
  7. washThe organic solution is washed with water
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-bd84b90d5ca542f285a9517cfa559188
出典データセット
uspto-grants-2009_09
特許番号
US07582627B2

関連ノート

読み込み中…