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

HRID 4228

Reaction equation

HRID 4228 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1bbdfdf4f42246edb2dbfdf161a6a0b2
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Linked notes

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