Oxalic Acid → HCID 23047471, compound

HRID 2107074Notes

Reaction equation

HRID 2107074 reaction equation
[C:1](=[N:5][OH:6])([NH2:4])[CH2:2][CH3:3].C1(N=C=NC2CCCCC2)CCCCC1.[Cl-].[C:23]([C:26]1[CH2:31][CH2:30][NH+:29]([CH3:32])[CH2:28][CH:27]=1)([OH:25])=O.[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35]>CN(C=O)C.C(O)C>[C:33]([O-:38])(=[O:37])[C:34]([O-:36])=[O:35].[CH3:32][NH+:29]1[CH2:30][CH2:31][C:26]([C:23]2[O:6][N:5]=[C:1]([CH2:2][CH3:3])[N:4]=2)=[CH:27][CH2:28]1.[CH3:32][NH+:29]1[CH2:30][CH2:31][C:26]([C:23]2[O:25][N:5]=[C:1]([CH2:2][CH3:3])[N:4]=2)=[CH:27][CH2:28]1

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 10868DicyclohexylcarbodiimideHCID 4092053N-HydroxypropionimidamideHCID 23047528HCID 23047528, compound

Product 1

HCID 23047471HCID 23047471, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Propionamide oxime (440 mg; 5,0 mmol), dicyclohexylcarbodiimide (1030 mg; 5.0 mmol) and 4-carboxy-1-methyl-1,2,5,6-tetrahydropyridinium chloride (886 mg; 5,0 mmol) were mixed in distilled DMF. The mixture was stirred at 60° C. for 1 1/2 hours and evaporated in vacuo. To the residue was added water (50 ml) and the mixture was extracted with toluene (3×75 ml). pH was adjusted to 10 by means of 4N NaOH and extracted with toluene (3×100 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo. Upon dissolving the residue in ethanol (99.9%) (5 ml) a solution of oxalic acid (360 mg; 4,0 mmol) in ethanol (99,9%) (5 ml) was added. Crystallization gave the title compound in 15% yield. M.P. 170°-171° C.

Workup

  1. customevaporated in vacuo
  2. additionTo the residue was added water (50 ml)
  3. extractionthe mixture was extracted with toluene (3×75 ml)
  4. extractionextracted with toluene (3×100 ml)
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customevaporated in vacuo
  7. additionwas added
  8. customCrystallization

Sources & evidence

ORD record
ord-2c5f5e9013e4430ea7d446d37fbd1f91
Source dataset
uspto-grants-1990_06
Patent number
US04933353

Reaction notes

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