Oxalic Acid → HCID 178465685, compound

HRID 1067721Notes

Reaction equation

HRID 1067721 reaction equation
Cl.[NH2:2][OH:3].C([O-])(=O)C.[Na+].[C:9]([C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][CH:26]=1)[O:15][CH2:16][CH2:17][CH2:18][C:19]1[N:20]=[CH:21][NH:22][CH:23]=1)(=O)[CH3:10].[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29]>O.C(O)C.CC(O)C.C(OCC)C>[C:27]([OH:32])(=[O:31])[C:28]([OH:30])=[O:29].[OH:3][N:2]=[C:9]([C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][CH:26]=1)[O:15][CH2:16][CH2:17][CH2:18][C:19]1[N:20]=[CH:21][NH:22][CH:23]=1)[CH3:10]

Participants

9

Reactant 4

HCID 971Oxalic AcidHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 178466643HCID 178466643, compound

Product 1

HCID 178465685HCID 178465685, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent2×

Procedure

A solution of 0.125 g (1.81 mmol) of hydroxylamine hydrochloride and 0.5 g (0.006 mol) of sodium acetate in 10 ml of water is stirred for 10 minutes, and a solution of 0.125 g (0.512 mmol) of 4-[3-(3-ethanoylphenoxy)propyl]-1H-imidazole in 3 ml of ethanol is then added slowly. The mixture is stirred at room temperature for 1 hour and then heated at 80° C. for 2 hours. After cooling, the solvent is removed under reduced pressure and the white residue obtained is extracted with chloroform. The chloroform is dried (MgSO4) and then evaporated. The oil obtained is dissolved in 4 ml of 2-propanol and treated with 1.3 equivalents of oxalic acid in 3 ml of 2-propanol. The addition of diethyl ether yields the product, which is separated by filtration, washed with ether and recrystallized in a 2-propanol/diethyl ether mixture, m.p. 149-151° C.

Workup

  1. temperatureheated at 80° C. for 2 hours
  2. temperatureAfter cooling
  3. customthe solvent is removed under reduced pressure
  4. customthe white residue obtained
  5. extractionis extracted with chloroform
  6. dry with materialThe chloroform is dried (MgSO4)
  7. customevaporated
  8. customThe oil obtained
  9. customyields the product, which
  10. customis separated by filtration
  11. washwashed with ether
  12. customrecrystallized in a 2-propanol/diethyl ether mixture, m.p. 149-151° C.

Sources & evidence

ORD record
ord-792d3f31801446b492d7c8c1382c4a29
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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