Citric Acid → N-[2-(Diethylamino)ethyl]-N-methyl-N'-(1-methylethyl)-N'-[2-(phenylsulfonyl)ethyl]urea citrate hydrate

HRID 4228

Reaktionsgleichung

Reaktionsgleichung von HRID 4228
[CH3:1][CH:2]([N:4]([CH2:8][CH2:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:12])=[O:11])[C:5](Cl)=[O:6])[CH3:3].[CH2:19]([N:21]([CH2:26][CH3:27])[CH2:22][CH2:23][NH:24][CH3:25])[CH3:20].C(N(CC)CC)C.[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>[OH2:6].[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].[CH2:19]([N:21]([CH2:26][CH3:27])[CH2:22][CH2:23][N:24]([CH3:25])[C:5]([N:4]([CH:2]([CH3:3])[CH3:1])[CH2:8][CH2:9][S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(=[O:12])=[O:11])=[O:6])[CH3:20]

Komponenten

8

Edukt 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 660341,2-Ethanediamine, N1,N1-diethyl-N2-methyl-HCID 13655164N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]carbamic chloride

Produkt 1

HCID 70419038N-[2-(Diethylamino)ethyl]-N-methyl-N'-(1-methylethyl)-N'-[2-(phenylsulfonyl)ethyl]urea citrate hydrate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 6.65 g (0.023 mole) of N-(1-methylethyl)-N-[2-(phenylsulfonyl)ethyl]carbamic chloride; 3.0 g (0.023 mole) of N,N-diethyl-N'-methylethylenediamine and triethylamine (2.7 g, 0.0267 mole) in 400 ml of tetrahydrofuran was stirred at room temperature for 10 hr. The solvent was removed in vacuo, and the residue was dissolved in a 60/40 mixture of ether and methylene chloride. This solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. This was dissolved in methanol, an excess of citric acid was added, and ether was added. A solid precipitated to give 11.08 g (82.4%) of white, crystalline solid; m.p. 77°-82° C.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in a 60/40 mixture of ether and methylene chloride
  3. extractionThis solution was extracted with several portions of water
  4. dry with materialwas dried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customto give an oil
  7. customA solid precipitated
  8. customto give 11.08 g (82.4%) of white, crystalline solid

Quellen und Nachweise

ORD-Eintrag
ord-1bbdfdf4f42246edb2dbfdf161a6a0b2
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04724235

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