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

HRID 4214

반응식

HRID 4214 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bfa7dcd3f23744c99a5e0a575455a555
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04724235

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