Oxalic acid dihydrate → HCID 10632607, compound

HRID 1600752Notes

Reaction equation

HRID 1600752 reaction equation
[CH2:1]([C:3]1[C:8]([CH2:9][CH3:10])=[CH:7][C:6]([NH2:11])=[C:5]([NH2:12])[CH:4]=1)[CH3:2].O.O.[C:15](O)(=[O:19])[C:16](O)=[O:17]>Cl>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:6](=[CH:7][C:8]=1[CH2:9][CH3:10])[NH:11][C:16](=[O:17])[C:15](=[O:19])[NH:12]2)[CH3:2]

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 220965954,5-Diethylbenzene-1,2-diamine

Product 1

HCID 10632607HCID 10632607, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
67.5 °C

Procedure

4,5-Diethyl-1,2-diaminobenzene (24 ) (459 mg, 2.80 mmol) was dissolved in 4 N hydrochloric acid (12 mL) at 90° C. Oxalic acid dihydrate (983 mg, 6.47 mmoL) was added to this solution in one portion with stirring under N2. The mixture was refluxed at 130-5° C. (oil bath) for 3 h. A yellow solid precipitated, which was collected by suction filtration and dried in vacuo overnight, giving 538 mg (88%) of the title compound 25 as a brown solid; mp>360° C.; 1H NMR (DMSO-d6, 300 MHz) δ 1.092 (t, 6H, J=7.5 Hz), 2.510 (q, 4H, J=7.5 Hz), 6.867 (s, 2H), 11.742 (s, 2H). EIMS m/e 218 (95, M+), 203 (100, M+ --CH3). (HPLC purity 100%)

Workup

  1. customA yellow solid precipitated
  2. filtrationwhich was collected by suction filtration
  3. customdried in vacuo overnight

Sources & evidence

ORD record
ord-4c4165caee2e47e39fc44304b44c6c58
Source dataset
uspto-grants-1999_11
Patent number
US05977107

Reaction notes

Loading…