1,1'-Carbonyldiimidazole → N-(1-Methylethyl)-N'-[2-[methyl-(2-phenylethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea hemihydrate

HRID 4214

反応式

HRID 4214 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=[O:2].[CH3:13][N:14]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:15][CH2:16][NH2:17].[CH3:26][CH:27]([NH:29][CH2:30][CH2:31][S:32]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH3:28].C[C:42](C)=[O:43].[C:45](OCC)(=[O:47])C>O1CCCC1.CCOCC>[OH2:2].[CH3:28][CH:27]([N:29]([CH2:30][CH2:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:33])=[O:34])[C:42]([NH:17][CH2:16][CH2:15][N:14]([CH3:13])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:43])[CH3:26].[CH3:28][CH:27]([N:29]([CH2:30][CH2:31][S:32]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)(=[O:33])=[O:34])[C:45]([NH:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:13])=[O:47])[CH3:26]

参加物

7

反応物 4

HCID 682631,1'-CarbonyldiimidazoleHCID 12488261N-Methyl-N-(2-phenylethyl)ethane-1,2-diamineHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamineHCID 21584569Ethylacetate acetone

生成物 1

HCID 70419535N-(1-Methylethyl)-N'-[2-[methyl-(2-phenylethyl)amino]ethyl]-N-[2-(phenylsulfonyl)ethyl]urea hemihydrate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1,1'-carbonyldiimidazole (8.12 g, 0.05 mole) and N-methyl-N-(2-phenylethyl)-1,2-ethanediamine, 8.0 g (0.0045 mole) in 300 ml of tetrahydrofuran was stirred for 2 hours at room temperature. To the mixture was added 9.37 g (0.0412 mole) of 1-methyl-N-[2-(phenylsulfonyl)ethyl]ethanamine and the reaction was heated at gentle reflux overnight. The reaction was stripped to dryness and dissolved in chloroformdiethyl ether (50-50 v/v) and extracted with water. The organic phase was extracted with 1N sulfuric acid. (Approximately half the product was extracted with acid and half remained in the organic layer). The oganic layer was extracted with dilute sodium hydroxide, dried, filtered, and the solvent removed to give an oil. The oil was subjected to column chromatography on Silica Gel using acetone-ethyl acetate as a eluant. This furnished 0.5 g (2.8%) of oil.

後処理

  1. temperaturethe reaction was heated
  2. temperatureat gentle reflux overnight
  3. extractionextracted with water
  4. extractionThe organic phase was extracted with 1N sulfuric acid
  5. extraction(Approximately half the product was extracted with acid and half
  6. extractionThe oganic layer was extracted with dilute sodium hydroxide
  7. customdried
  8. filtrationfiltered
  9. customthe solvent removed
  10. customto give an oil

出典と根拠

ORDレコード
ord-bfa7dcd3f23744c99a5e0a575455a555
出典データセット
uspto-grants-1988_02
特許番号
US04724235

関連ノート

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