Hydrochloric Acid → HCID 178438840, compound

HRID 1947178Notes

Reaction equation

HRID 1947178 reaction equation
[CH:1]([C:4]1[C:5]([O:33]COC)=[CH:6][C:7]([O:29]COC)=[C:8]([C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:18][CH:17]=3)[C:12](=[S:15])[NH:13][N:14]=2)[CH:9]=1)([CH3:3])[CH3:2].Cl.[OH-].[Na+]>C(O)C>[CH:1]([C:4]1[CH:9]=[C:8]([C:10]2[N:11]([C:16]3[CH:21]=[CH:20][C:19]([CH2:22][N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:18][CH:17]=3)[C:12]([SH:15])=[N:13][N:14]=2)[C:7]([OH:29])=[CH:6][C:5]=1[OH:33])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59829782HCID 59829782, compound

Product 1

HCID 178438840HCID 178438840, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Crystals of 5-(5-isopropyl-2,4-bis-methoxymethoxy-phenyl)-4-[4-(morpholin-4-ylmethyl)-phenyl]-2,4-dihydro-[1,2,4]triazol-3-thione (IM6-S-a02) (1.43 g, 2.77 mmol) and a mixed solvent of 5.0 N aqueous hydrochloric acid (15 mL) and ethanol (15 mL) were placed in a 100 mL eggplant shaped flask and stirred at room temperature for 3.5 hours. After completing the reaction, the reaction mixture was neutralized with 5 N aqueous sodium hydroxide and then extracted with ethyl acetate. After drying over anhydrous sodium sulfate the collected organic layer was concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography to obtain the title compound (SH-a02: 647 mg, 54.7%).

Workup

  1. customthe reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialAfter drying over anhydrous sodium sulfate the collected organic layer
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-55ebd58cc4174ac1af246539a2544542
Source dataset
uspto-grants-2013_03
Patent number
US08399464B2

Reaction notes

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