Sodium Hydroxide → HCID 18399615, compound

HRID 381283Notes

Reaction equation

HRID 381283 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:7][C:6]2[C:16]([C:19]([O:21]C)=[O:20])=[CH:17][S:18][C:5]1=2>CO.O1CCOCC1.O>[O:3]=[C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[O:7][C:6]2[C:16]([C:19]([OH:21])=[O:20])=[CH:17][S:18][C:5]1=2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 22464455HCID 22464455, compound

Product 1

HCID 18399615HCID 18399615, compoundYield 93.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
22.5 °C

Procedure

26 mL of 0.6N sodium hydroxide was added to a solution of 3.82 g of Compound 1F in 174 mL of methanol and 87 mL of dioxane at 50° C. while stirring. The mixture was stirred at 50° C. for an additional 20 minutes, cooled to 20-25° C., then diluted with 280 mL of water, filtered and acidified with 1N hydrochloric acid to pH=1. The suspension of that formed precipitate gel was stirred at 60° C. for 2 hours, until a heavier filtrable solid was obtained. This solid was filtered and dried to yield 3.4 g of the title compound, which was suitable for use in the next reaction step without further purification. It was crystallized from ethanol to yield the analytical sample, melting at 282-283° C.

Workup

  1. stirringThe mixture was stirred at 50° C. for an additional 20 minutes
  2. filtrationfiltered
  3. additionThe suspension of
  4. customthat formed precipitate gel
  5. stirringwas stirred at 60° C. for 2 hours, until a heavier filtrable solid
  6. customwas obtained
  7. filtrationThis solid was filtered
  8. customdried

Sources & evidence

ORD record
ord-3964ff349f3e48e8bc094f0c4a4383dd
Source dataset
uspto-grants-2001_10
Patent number
US06306861B1

Reaction notes

Loading…