Hydrochloric Acid → HCID 22097040, compound

HRID 1458559Notes

Reaction equation

HRID 1458559 reaction equation
[Cl:1][C:2]1[C:3]([N:17]([CH:22]([C:24]([O:26]C)=[O:25])[CH3:23])[S:18]([CH3:21])(=[O:20])=[O:19])=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13]C)[C:6]([O:15]C)=[N:5]2.Cl>O1CCOCC1>[C:24]([CH:22]([N:17]([C:3]1[C:2]([Cl:1])=[C:11]([Cl:12])[CH:10]=[C:9]2[C:4]=1[NH:5][C:6](=[O:15])[C:7](=[O:13])[NH:8]2)[S:18]([CH3:21])(=[O:19])=[O:20])[CH3:23])([OH:26])=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22097002HCID 22097002, compound

Product 1

HCID 22097040HCID 22097040, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A 1:1 mixture of the two isomers of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(1 -methoxycarbonyl- 1-ethyl)-methanesulphonamide (Preparation 23, 1.40 g, 32 mmol), 2M hydrochloric acid (40 ml) and dioxane (40 ml) was heated in an autoclave at 130° C. for 48 h and 150° C. for 24 h. The mixture was cooled, concentrated to low volume under reduced pressure and the solid filtered off and washed with ether. The product was dissolved in 1M aqueous sodium hydroxide (40 ml) and precipitated by the addition of 2M hydrochloric acid (to pH3). The white solid was filtered off and dried in vacuo, to give the title compound (1.13 g, 89%), as a mixture of diastereomers, m.p. 282° C. (dec).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated to low volume under reduced pressure
  3. filtrationthe solid filtered off
  4. washwashed with ether
  5. dissolutionThe product was dissolved in 1M aqueous sodium hydroxide (40 ml)
  6. customprecipitated by the addition of 2M hydrochloric acid (to pH3)
  7. filtrationThe white solid was filtered off
  8. customdried in vacuo

Sources & evidence

ORD record
ord-979669467829439995022db94c9aa8b7
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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