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Dimethyl Sulfoxide → trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetaldehyde

HRID 1786
ノート
印刷プレビュー

反応式

HRID 1786 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69945311trans-7-Chloro-5-(2-chlorophenyl)-1-isopropyl-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-ethanol

生成物 1

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

試薬・触媒・溶媒

1
HCID 6344Dichloromethane溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-848ec5bd613e4f5c9be2f2b670bc528c
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05726306

反応ノート

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