Dichloromethane → 1,10-Bis(3',5'-dimethyl-4'-acetoxyphenylcarbonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane

HRID 2288251ノート

反応式

HRID 2288251 の反応式
C(Cl)Cl.[CH3:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH3:18])[C:13]=1[O:14][C:15](=[O:17])[CH3:16])[C:8](Cl)=[O:9].[NH:19]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][NH:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(N([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44]N=1)CC)C>C(N(CC)CC)C>[CH3:4][C:5]1[CH:6]=[C:7]([C:8]([N:19]2[CH2:36][CH2:35][O:34][CH2:33][CH2:32][O:31][CH2:30][CH2:29][N:28]([C:8]([C:7]3[CH:11]=[C:47]([CH3:42])[C:46]([O:17][C:15](=[O:14])[CH3:16])=[C:45]([CH3:44])[CH:6]=3)=[O:9])[CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[O:9])[CH:11]=[C:12]([CH3:18])[C:13]=1[O:14][C:15](=[O:17])[CH3:16]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 72805Diaza-18-crown-6HCID 232542N,N-Diethylpyridin-2-amineHCID 18704177Acetic acid 4-chlorocarbonyl-2,6-dimethyl-phenyl ester

生成物 1

HCID 187041651,10-Bis(3',5'-dimethyl-4'-acetoxyphenylcarbonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane収率 570.5%

試薬・触媒・溶媒 1

HCID 8471Triethylamine溶媒

実験手順

To 50 ml of methylene chloride were dissolved 0.9 g/4 mmol of 3,5-dimethyl-4-acetoxybenzoyl chloride and 0.5 g/1.9 mmol of 1,10-diaza-4,7,13,16-tetraoxacyclooctadecane, and to this solution was added 2.2 ml of triethylamine and a catalytic amount (40 mg/0.3 mmol) of diethylaminopyridine in an ice bath. The reaction mixture was refluxed under heat for 4 hours, and allowed to cool to room temperature. The reaction solution was washed with 1N hydrochloric acid, distilled water, saturated aqueous solution of sodium hydrogencarbonate, and saturated aqueous solution of sodium chloride, in this order. The organic layer was dried with anhydrous sodium sulfate, and after removing the drying agent, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using methylene chloride-methanol for the eluting solution to obtain 1.1 g of the desired 1,10-bis(3',5'-dimethyl-4'-acetoxyphenylcarbonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane. MS: 642 (M+), 451, 191. 1H-NMR (CDCl3): δ2.15 (6H, s), 2.34 (12H, s), 3.6 (16H, br), 3.8 (8H, br), 7.05 (4H, s).

後処理

  1. temperatureThe reaction mixture was refluxed
  2. temperatureunder heat for 4 hours
  3. washThe reaction solution was washed with 1N hydrochloric acid
  4. distillationdistilled water, saturated aqueous solution of sodium hydrogencarbonate, and saturated aqueous solution of sodium chloride
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. customafter removing the drying agent
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-6464eb73e114421abb671e9bf2ff902f
出典データセット
uspto-grants-2000_07
特許番号
US06087502

反応ノート

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