Oxalic acid dihydrate → HCID 178481712, compound

HRID 1031087Notes

Reaction equation

HRID 1031087 reaction equation
[NH2:1][C:2]1[C:10]2[C:6](=[N:7][N:8]([CH3:11])[N:9]=2)[CH:5]=[CH:4][C:3]=1[NH2:12].O.O.[C:15](O)(=[O:19])[C:16](O)=[O:17]>Cl>[OH:17][C:16]1[C:15]([OH:19])=[N:1][C:2]2[C:10]3=[N:9][N:8]([CH3:11])[N:7]=[C:6]3[CH:5]=[CH:4][C:3]=2[N:12]=1

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 19915804HCID 19915804, compound

Product 1

HCID 178481712HCID 178481712, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4,5-diamino-2-methylbenzotriazole (2.5 g, 15.3 mmol) and oxalic acid dihydrate (2.5 g, 19.8 mmol) in 80 ml of 4M hydrochloric acid was refluxed on an oil bath for 1 h. The cooled mixture was filtered, and the precipitate was washed with water and ethanol. Recrystallization from ethanol with decolourising charcoal afforded 1.0 g (30%) of the title compound; m.p. >300° C.; IR (KBr): 3500- 2200, 1690 cm-1 ; 1H-NMR (DMSO-d6): 4.48 (s, 3H, CH3), 7.25 (d, J=9 Hz, 1H, ArH), 7.60 (d, J=9 Hz, 1H, ArH), 12.03 (broad s, 1H, OH), 12.47 (broad s, 1H, OH).

Workup

  1. filtrationThe cooled mixture was filtered
  2. washthe precipitate was washed with water and ethanol
  3. customRecrystallization from ethanol with decolourising charcoal

Sources & evidence

ORD record
ord-d3813340fc5f4be484356c9076b89c18
Source dataset
uspto-grants-1992_04
Patent number
US05109001

Reaction notes

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