Citric Acid → N-[2-(Diethylamino)ethyl]-N-ethyl-N'-[2-(phenylsulfonyl)ethyl]urea citrate

HRID 4216

반응식

HRID 4216 반응식
[C:1]1([S:7]([CH2:10][CH2:11][NH2:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](N1C=CN=C1)(N1C=CN=C1)=[O:14].[CH2:25]([N:27]([CH2:33][CH3:34])[CH2:28][CH2:29][NH:30][CH2:31][CH3:32])[CH3:26].[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38]>O1CCCC1.CO.CCOCC>[C:35]([OH:47])(=[O:46])[CH2:36][C:37]([CH2:42][C:43]([OH:45])=[O:44])([C:39]([OH:41])=[O:40])[OH:38].[CH2:25]([N:27]([CH2:33][CH3:34])[CH2:28][CH2:29][N:30]([CH2:31][CH3:32])[C:13]([NH:12][CH2:11][CH2:10][S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)(=[O:8])=[O:9])=[O:14])[CH3:26]

참가 물질

8

반응물 4

HCID 311Citric AcidHCID 66040TriethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 35454972-(Benzenesulfonyl)ethan-1-amine

생성물 1

HCID 13655129N-[2-(Diethylamino)ethyl]-N-ethyl-N'-[2-(phenylsulfonyl)ethyl]urea citrate수율 52%

시약·촉매·용매 3

HCID 887Methanol용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 5.55 g (0.030 mole) of 2-(phenylsulfonyl)ethanamine and 5.35 g (0.033 mole) of 1,1'-carbonyldiimidazole in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 4.62 g (0.032 mole) of N,N,N'-triethylethylenediamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 16 hr. The solvent was removed in vacuo, and the residue was partitioned between a mixture of 300 ml of methylene chloride and 500 ml of ether and water. The organic phase was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. A solution of the oil in methanol was treated with an equivalent of citric acid and ether was added. A white precipitate formed to give 8.54 g (52.0%) of white crystalline solid, m.p. 105°-107° C.

후처리

  1. temperaturethe mixture was refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between a mixture of 300 ml of methylene chloride and 500 ml of ether and water
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. additionwas added
  8. customA white precipitate formed

출처 및 근거

ORD 기록
ord-fefe59a7cdf245f1bf02e5ac9fe770f6
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04724235

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