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

HRID 10338

反应方程式

HRID 10338 反应方程式
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>[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]

参与物

7

反应物 5

HCID 313海萝胶HCID 2707水合氯醛HCID 62649Sodium sulfate decahydrateHCID 443297盐酸羟胺HCID 102197187,8-Difluoro-2,3-dihydro-3-methyl-4H-(1,4)benzoxazine

产物 1

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

试剂、催化剂与溶剂 1

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂2 次

反应条件

温度
77.5 °C

实验过程

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.

后处理

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

来源与证据

ORD记录
ord-b845dd2edd604c6ea501e182a83263a2
来源数据集
uspto-grants-2006_08
专利号
US07094780B1

关联笔记

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