HCID 19990456, compound → HCID 19990431, compound

HRID 346164Notes

Reaction equation

HRID 346164 reaction equation
C([NH:8][S:9]([C:12]1[CH:21]=[C:20]2[C:15]([NH:16][C:17](=[O:24])[C:18](=[O:23])[N:19]2[OH:22])=[CH:14][C:13]=1[C:25]([F:28])([F:27])[F:26])(=[O:11])=[O:10])(C(OCC)=O)=O>Cl>[OH:22][N:19]1[C:20]2[C:15](=[CH:14][C:13]([C:25]([F:28])([F:27])[F:26])=[C:12]([S:9](=[O:11])(=[O:10])[NH2:8])[CH:21]=2)[NH:16][C:17](=[O:24])[C:18]1=[O:23]

Participants

3

Reactant 1

HCID 19990456HCID 19990456, compound

Product 1

HCID 19990431HCID 19990431, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 7-ethoxalylaminosulfonyl-1-hydroxy-6-trifluoromethylquinoxaline-2,3(1H,4H)-dione (12.0 g, 28 mmol) in 150 ml of 1M hydrochloric acid was heated at reflux for 2 h with stirring. The cooled mixture was filtered and the isolated solid was washed with water and light petroleum. The crude product was recrystallized from water with decolourizing charcoal and dried in vacuo over phosphorous pentoxide for 3 h to give 7.1 g (77%) of the pure title compound. M.p. 296° C. decomp. (DSC); IR (KBr): 1700, 1615 cm-1 ; 1H-NMR (DMSO-d6): 7.67 (s, 1H, ArH), 7.77 (s, 2H, NH2), 8.26 (s, 1H, ArH), 12.2 (broad s, 2H, NH and OH); MS m/e: 325 (M+, 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. filtrationThe cooled mixture was filtered
  4. washthe isolated solid was washed with water and light petroleum
  5. customThe crude product was recrystallized from water with decolourizing charcoal
  6. dry with materialdried in vacuo over phosphorous pentoxide for 3 h

Sources & evidence

ORD record
ord-cff2fe22ce8a4708a722d35053ce5ef8
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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