Hydrochloric Acid → HCID 10643735, compound

HRID 2181165Notes

Reaction equation

HRID 2181165 reaction equation
[OH-:1].[Na+].N1(C(=S)C[C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:27]=[CH:26][C:25]4[C:20](=CC=CC=4)[C:19]=3OC3C(OCC4C=CC=CC=4)=CC=CC=3)=[CH:13][CH:12]=2)CCOCC1.Cl.[CH2:45]([OH:47])[CH3:46]>>[CH2:45]([O:47][C:11]1[CH:12]=[C:25]2[C:20](=[CH:15][CH:16]=1)[CH:19]=[C:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:13][C:14]([OH:17])=[O:1])=[CH:16][CH:15]=1)[CH:27]=[CH:26]2)[C:46]1[CH:20]=[CH:19][CH:18]=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 22484875HCID 22484875, compound

Product 1

HCID 10643735HCID 10643735, compoundYield 69%

Conditions

Temperature
100 °C

Procedure

An aqueous solution (10 ml) of 50% sodium hydroxide was added to 70% ethanol solution (50 ml) of the 1-(morpholin-4-yl)-2-(4-(6-benzyloxyphenoxy-2-naphthyloxy)phenyl)-ethane-thione (3.73 g, 7.94 mmol) obtained by the Reference Example 3 and the mixture was stirred at 100° C. for a night. After completing the reaction, the reaction liquid was added with 6N hydrochloric acid to adjust the pH to about 2, extracted with ethyl acetate, washed with water, dried with magnesium sulfate and concentrated. The obtained crude product was recrystallized from acetonitrile to obtain the subject compound (2.10 g, 5.46 mmol). The result of 1H-NMR was consistent with the above structure.

Workup

  1. customobtained by the Reference Example 3
  2. customthe reaction
  3. customthe reaction liquid
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customThe obtained crude product
  9. customwas recrystallized from acetonitrile

Sources & evidence

ORD record
ord-eb176f9b960a43e8b9bce62776ba554e
Source dataset
uspto-grants-2005_05
Patent number
US06890932B2

Reaction notes

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