Dimethyl Sulfoxide → [4-(4-Benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanone

HRID 571782ノート

反応式

HRID 571782 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:23][CH2:22][O:21][CH:20]([C:24]2[CH:29]=[CH:28][C:27]([CH:30]([C:32]3[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:39])[OH:31])=[CH:26][CH:25]=2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(CC)CC.[NH4+].[OH-]>C(Cl)Cl>[CH2:11]([N:18]1[CH2:23][CH2:22][O:21][CH:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([C:32]3[C:37]([CH3:38])=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:39])=[O:31])=[CH:26][CH:25]=2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

7

反応物 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 66653558HCID 66653558、化合物

生成物 1

HCID 66653880[4-(4-Benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanone収率 94.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of oxalyl chloride (0.46 mL, 5.4 mmol) in CH2Cl2 (20 mL), was added dropwise DMSO (0.94 mL, 13.2 mmol), at −78° C. Subsequently, a solution of [4-(4-benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanol (1.6 g, 4.1 mmol) in CH2Cl2 (30 mL) was added, dropwise, at −78° C. After the addition was complete the mixture was stirred for 30 min., at −78° C., and then Et3N (2.9 mL, 20.8 mmol) was added. After complete addition the mixture was allowed to warm to room temperature, overnight. Next, a 2M aqueous NH4OH solution (30 mL) was added, and the mixture extracted with CH2Cl2. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford [4-(4-benzyl-morpholin-2-yl)-phenyl]-(2,6-dimethyl-phenyl)-methanone (1.5 g), which was used as such in the next step.

後処理

  1. customat −78° C
  2. customat −78° C
  3. additionAfter the addition
  4. additionAfter complete addition the mixture
  5. temperatureto warm to room temperature, overnight
  6. extractionthe mixture extracted with CH2Cl2
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4fe5b31e0c144ccfa480ff75df54ac30
出典データセット
uspto-grants-2015_05
特許番号
US09029371B2

反応ノート

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