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

HRID 4216
ノート
印刷プレビュー

反応式

HRID 4216 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887
Methanol
溶媒
HCID 3283Diethyl Ether溶媒
HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fefe59a7cdf245f1bf02e5ac9fe770f6
出典データセット
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04724235

反応ノート

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