Hydrochloric Acid → Tetomilast

HRID 2283519Notes

Reaction equation

HRID 2283519 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[N:23]=[C:22]([C:24]([O:26]C)=[O:25])[CH:21]=[CH:20][CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[OH-].[Na+].C(O)C.Cl>O.C(OCC)(=O)C>[CH3:12][CH2:11][O:10][C:9]1[CH:8]=[CH:7][C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([C:24]([OH:26])=[O:25])[N:23]=3)[N:17]=2)=[CH:5][C:4]=1[O:3][CH2:1][CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 10385338HCID 10385338, compound

Product 1

HCID 3025803Tetomilast

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

First, methyl 6-[2-(3,4-diethoxyphenyl)thiazol-4-yl]pyridin-2-carboxylate (49 g; 127 mmol) and 10% sodium hydroxide (100 ml) were added to ethanol (1.4 L), and the obtained mixture was then stirred for 4 hours under heating to reflux. A majority of solvent was eliminated from the obtained solution, and water and ethyl acetate were then added to the residue for separation. The water layer obtained as a result of the separation was changed to acidic by addition of 10% hydrochloric acid, followed by extraction with ethyl acetate. Thereafter, the extract was quickly washed with a saturated sodium chloride aqueous solution, and was then dried over an excessive amount of magnesium sulfate. The obtained mixture was recrystallized from ethyl acetate, so as to obtain an anhydrous tetomilast type B crystal.

Workup

  1. temperatureunder heating to reflux
  2. additionwere then added to the residue for separation
  3. customa result of the separation
  4. extractionfollowed by extraction with ethyl acetate
  5. washThereafter, the extract was quickly washed with a saturated sodium chloride aqueous solution
  6. dry with materialwas then dried over an excessive amount of magnesium sulfate
  7. customThe obtained mixture was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ba2f7ce34e5e49f491e627b65d97a2ab
Source dataset
uspto-grants-2015_09
Patent number
US09145404B2

Reaction notes

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