Hydrochloric Acid → HCID 10643735, compound

HRID 480263Notes

Reaction equation

HRID 480263 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-1-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-f526a5f6805842238672f000b20e6ab5
Source dataset
uspto-grants-2003_11
Patent number
US06649656B1

Reaction notes

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