二甲基亚砜 → trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde

HRID 1786

反应方程式

HRID 1786 反应方程式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH:22]([CH3:24])[CH3:23])[C:20](=[O:25])[C@@H:19]([CH2:26][CH2:27][OH:28])[O:18][C@H:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:16]=2[CH:36]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[N:21]([CH:22]([CH3:23])[CH3:24])[C:20](=[O:25])[C@@H:19]([CH2:26][CH:27]=[O:28])[O:18][C@H:17]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[Cl:35])[C:16]=2[CH:36]=1

参与物

6

反应物 4

HCID 679二甲基亚砜HCID 8471三乙胺HCID 65578草酰氯HCID 69945311trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol

产物 1

HCID 86752221trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde收率 92.5%

试剂、催化剂与溶剂 1

HCID 6344二氯甲烷溶剂3 次

实验过程

A solution of oxalyl chloride (0.72 ml) in methylene chloride (10 ml) was cooled to -65° C., to which was added dropwise a solution of dimethyl sulfoxide (0.63 ml) in methylene chloride (2 ml) taking 5 minutes, followed by stirring for 5 minutes. To the mixture was added dropwise, taking 15 minutes, a solution of trans-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol (2.5 g) obtained in Example 47 in methylene chloride (15 ml), which was stirred for 10 minutes. To the resultant mixture was added triethylamine (3.45 ml) taking 5 minutes, then the cooling bath was removed. The mixture was stirred for 10 minutes at room temperature, to which was then added 1N hydrochloric acid (50 ml), followed by stirring. The methylene chloride layer was dried over anhydrous magnesium sulfate, then the solvent was distilled off under reduced pressure to leave trans-7-chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde (2.3 g) as an oily product.

后处理

  1. additionTo the mixture was added dropwise
  2. waittaking 15 minutes
  3. waittaking 5 minutes
  4. customthe cooling bath was removed
  5. stirringThe mixture was stirred for 10 minutes at room temperature, to which
  6. additionwas then added 1N hydrochloric acid (50 ml)
  7. stirringby stirring
  8. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

来源与证据

ORD记录
ord-848ec5bd613e4f5c9be2f2b670bc528c
来源数据集
uspto-grants-1998_03
专利号
US05726306

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