Oxalic acid dihydrate → HCID 178514680, compound

HRID 1165819Notes

Reaction equation

HRID 1165819 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12](=[O:15])(=[O:14])[NH2:13])=[CH:4][C:3]=1[NH2:16].O.O.[C:19](O)(=[O:23])[C:20](O)=[O:21]>Cl>[OH:21][C:20]1[C:19]([OH:23])=[N:16][C:3]2[CH:4]=[C:5]([S:12](=[O:15])(=[O:14])[NH2:13])[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 114021381-Naphthalenesulfonamide, 3,4-diamino-

Product 1

HCID 178514680HCID 178514680, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1.0 g (3.4 mmol) 1,2-diamino-4-sulphamoyl-naphtalene and 1.0 (7.9mmol) oxalic acid dihydrate in 20 ml 2N HCl was refluxed for 2 hours. After cooling to room temperature the precipitate was filtered off and washed with water. The crude product was recrystallized from dimethylformamide/water to give 0.6g(50%) of the title compound, M.p. > 300° C., H NMR (DMSO-d6): 1.22(2H,s), 8.7(2H,m), 8.2(1H,s), 7.7-(4H,m).

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationwas filtered off
  3. washwashed with water
  4. customThe crude product was recrystallized from dimethylformamide/water

Sources & evidence

ORD record
ord-9802e8bfee214215ab34b2dddcef7932
Source dataset
uspto-grants-1990_03
Patent number
US04912108

Reaction notes

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