Hydrochloric Acid → HCID 22041793, compound

HRID 1791081Notes

Reaction equation

HRID 1791081 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([Cl:25])=[C:20]([CH:24]=3)[C:21]([OH:23])=[O:22])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1.Cl.[CH3:27]O>O1CCOCC1>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([S:12]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([Cl:25])=[C:20]([CH:24]=3)[C:21]([O:23][CH3:27])=[O:22])(=[O:14])=[O:13])=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 22041797HCID 22041797, compound

Product 1

HCID 22041793HCID 22041793, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 10.1 g (0.027 mol) of compound 133 dissolved in 250 mL of methanol was added 50 mL of 4 N HCl in dioxane. This solution was allowed to stir at ambient temperature for 18 hours. The reaction was incomplete, so it was heated at reflux for an additional 5 hours. Then, the volatiles were removed by rotary evaporation and the resulting solid was extracted with ethyl acetate and 0.4 N sodium bicarbonate, water, and brine. The organic layer was dried (MgSO4), filtered, and the volatiles removed by rotary evaporation to yield 8.71 g of compound 134.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for an additional 5 hours
  3. customThen, the volatiles were removed by rotary evaporation
  4. extractionthe resulting solid was extracted with ethyl acetate and 0.4 N sodium bicarbonate, water, and brine
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. customthe volatiles removed by rotary evaporation

Sources & evidence

ORD record
ord-9d217d3fb93145c49068748249c315f8
Source dataset
uspto-grants-2006_07
Patent number
US07071231B2

Reaction notes

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