Oxalic Acid → HCID 19869466, compound

HRID 330416Notes

Reaction equation

HRID 330416 reaction equation
[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH2:6])[CH3:2].[C:9]1([S:15]([CH2:18][CH2:19][NH:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[CH2:35]([O:37]CC)C>O1CCCC1.CO>[OH2:16].[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[CH2:1]([N:3]([CH2:7][CH3:8])[CH2:4][CH2:5][NH:6][C:35](=[O:37])[N:20]([CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)[CH2:19][CH2:18][S:15]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)(=[O:16])=[O:17])[CH3:2]

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 3283Diethyl EtherHCID 60993N,N-DiethylethylenediamineHCID 14855232HCID 14855232, compound

Product 1

HCID 19869466HCID 19869466, compoundYield 66.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4.70 g (0.029 mole) of 1,1'-carboyldiimidazole and 3.14 g (0.027 mole) of N,N-diethylethylenediamine in 40 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 7.28 g (0.0244 mole) of N-[2-(phenylsulfonyl)ethyl]-4-morpholineethanamine 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 methylene chloride and water. The methylene chloride phase was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. The oil was dissolved in methanol, 2 equivalents of oxalic acid were added, and diethyl ether was added. A white solid precipitated to give 10.33 g (66.3%) of the title compound, a white crystalline solid, m.p. 98°-100° C.

Workup

  1. temperaturethe mixture was refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. customthe residue was partitioned between methylene chloride and water
  4. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  5. customthe solvent was removed in vacuo
  6. customto give an oil
  7. customA white solid precipitated

Sources & evidence

ORD record
ord-f3b342b865bc4de8bf8deab4c5dd7f6f
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

Loading…