1,1'-Carbonyldiimidazole → N'-[2-(Diethylamino)-1-methylethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea

HRID 745189

反応式

HRID 745189 の反応式
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH2:13]([N:15]([CH2:20][CH3:21])[CH2:16][CH:17]([NH2:19])[CH3:18])[CH3:14].[C:22]1([S:28]([CH2:31][CH2:32][NH:33][CH:34]([CH3:36])[CH3:35])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:13]([N:15]([CH2:20][CH3:21])[CH2:16][CH:17]([NH:19][C:1](=[O:2])[N:33]([CH:34]([CH3:36])[CH3:35])[CH2:32][CH2:31][S:28]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)(=[O:29])=[O:30])[CH3:18])[CH3:14]

参加物

5

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamineHCID 16643481(2-Aminopropyl)diethylamine

生成物 1

HCID 20152789N'-[2-(Diethylamino)-1-methylethyl]-N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]urea収率 59.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 12.15 g (0.075 mole) of 1,1'-carbonyl diimidazole and 7.50 g (0.0476 mole) of 1-diethylamino-2-propanamine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 12.26 g (0.054 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the solution was refluxed for 19 hr. The solvent was removed in vacuo, and the residue was dissolved in a 50/50 mixture of methylene chloride and ether. The organic solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (elution with methanol) gave 10.87 g (52.3 g) of clear colorless oil. 1H NMR (CDCl3)δ7.5-8.15 (m, s. aromatic), 5.35 (br s, 1, NH), 4.1 (m, 1, (CH3)2CH), 3.45-4.0 (m, 1. NHCH(CH3)CH2), 2.5-2.85 (m, 6, CH2CH3)), 0.85-1.3 (m, 15, CH3 groups).

後処理

  1. temperaturethe solution was refluxed for 19 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in a 50/50 mixture of methylene chloride and ether
  4. extractionThe organic solution was extracted with several portions of water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give an oil

出典と根拠

ORDレコード
ord-d6f7b9cd8a144e3088b7dc53097cca2d
出典データセット
uspto-grants-1986_07
特許番号
US04597902

関連ノート

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