Hydrochloric Acid → HCID 59179706, compound

HRID 2381842Notes

Reaction equation

HRID 2381842 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH:16]=[C:15]([CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:14]=[N:13]2)[S:5][C:6]=1[C:7]([O:9]CC)=[O:8].[OH-].[Li+].Cl>O1CCCC1.O>[CH3:1][C:2]1[N:3]=[C:4]([N:12]2[CH:16]=[C:15]([CH2:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:14]=[N:13]2)[S:5][C:6]=1[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59179696HCID 59179696, compound

Product 1

HCID 59179706HCID 59179706, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-methyl-2-(4-(3-phenylpropyl)-1H-1,2,3-triazol-1-yl)thiazole-5-carboxylate (7.04 g, 19.78 mmol) in a mixture of tetrahydrofuran (25 mL) and water (25 mL) was added lithium hydroxide (4.15 g, 98.90 mmol). The reaction mixture was stirred at ambient temperature 18 hours, acidified with 10% hydrochloric acid solution, and extracted with dichloromethane (2×100 μL). The organic layer was separated, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to afford the title compound in 89% yield (5.82 g): 1H NMR (300 MHz, DMSO-d6) δ 8.72 (s, 1H), 7.31-7.15 (m, 5H), 2.75-2.49 (m, 7H), 2.00-1.95 (m, 2H); MS (ES+) m/z 329.2 (M+1).

Workup

  1. extractionextracted with dichloromethane (2×100 μL)
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5355c7392b38472ba5ad21469d93b723
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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