Dimethyl Sulfoxide → 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanone

HRID 1257758ノート

反応式

HRID 1257758 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([S:17]([N:20]2[CH:31]=[CH:30][C:29]3[C:21]2=[N:22][CH:23]=[C:24]2[C:28]=3[N:27]([CH:32]3[CH2:37][CH2:36][CH:35]([OH:38])[CH2:34][CH2:33]3)[N:26]=[N:25]2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>ClCCl>[C:11]1([S:17]([N:20]2[CH:31]=[CH:30][C:29]3[C:21]2=[N:22][CH:23]=[C:24]2[C:28]=3[N:27]([CH:32]3[CH2:33][CH2:34][C:35](=[O:38])[CH2:36][CH2:37]3)[N:26]=[N:25]2)(=[O:18])=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 673454584-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanol

生成物 1

HCID 673431594-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanone収率 78.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-20 °C

実験手順

To a solution of oxalyl chloride (665.5 mg, 5.24 mmol) in anhydrous dichloromethane (40 mL) was added anhydrous dimethylsulfoxide (0.44 mL, 9.12 mmol) at −78° C. under nitrogen, followed by stirring for 15 minutes. Then the reaction temperature was warmed to −20° C. and a solution of 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanol (750 mg, 1.94 mmol) in anhydrous dichloromethane (10 mL)was added dropwise. The mixture was stirred at −20° C. for 15 minutes and warmed to room temperature. Triethylamine (2.15 g, 19.4 mmol) was added and the mixture was stirred for 90 minutes. The reaction mixture was quenched with water and extracted with ethyl acetate. The extracts were dried over sodium sulfate and concentrated under reduced pressure to give the crude product, which was crystallized form ethanol to give 600 mg (78%) of 4-(6-Benzenesulfonyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-cyclohexanone as a solid. 1H NMR (400 MHz, CDCl3) δ: 9.29 (s, 1H), 8.24-8.22 (m, 3H), 7.81-7.64 (m, 4H), 5.67-5.65 (m, 1H), 2.91-2.83 (m, 2H), 2.52-2.49 (m, 6H),

後処理

  1. stirringThe mixture was stirred at −20° C. for 15 minutes
  2. temperaturewarmed to room temperature
  3. stirringthe mixture was stirred for 90 minutes
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe extracts were dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product, which
  9. customwas crystallized form ethanol

出典と根拠

ORDレコード
ord-258aaff01879496694e770010a859b3a
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

反応ノート

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