Hydrochloric Acid → HCID 10388689, compound

HRID 1742645Notes

Reaction equation

HRID 1742645 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14]([CH:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][O:19][C:18]2[CH:27]=[CH:28][C:29]([C:31]([O:33]C)=[O:32])=[CH:30][C:17]1=2)=[O:15])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:31]([C:29]1[CH:28]=[CH:27][C:18]2[O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH:16]([C:14]([NH:13][C:5]3[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=[CH:7][C:6]=3[CH:10]([CH3:11])[CH3:12])=[O:15])[C:17]=2[CH:30]=1)([OH:33])=[O:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 3072813144170-16-12×

Product 1

HCID 10388689HCID 10388689, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

After 0.58 g of 6,11-dihydro-N-(2,6-diisopropylphenyl)-2-methoxycarbonyldibenz[b,e]oxepin-11-carboxamide (Compound 24) obtained in Example 24 was dissolved in 24 ml of methanol, 6 ml of 5N sodium hydroxide was added to the solution. The mixture was heated under reflux for 5 minutes. After completion of the reaction, the mixture was cooled to room temperature and 4N hydrochloric acid was added thereto to adjust pH to 3. The mixture was extracted with ethyl acetate. After washing with saturated sodium hydroxide aqueous solution, the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to dryness to obtain 0.52 g of Compound 25.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 5 minutes
  3. customAfter completion of the reaction
  4. extractionThe mixture was extracted with ethyl acetate
  5. washAfter washing with saturated sodium hydroxide aqueous solution
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure to dryness

Sources & evidence

ORD record
ord-2f5ff1a43e0242d4bb8bcbe75c6593f1
Source dataset
uspto-grants-1994_08
Patent number
US05340807

Reaction notes

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