Hydrochloric Acid → HCID 68492838, compound

HRID 2381848Notes

Reaction equation

HRID 2381848 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:20]=[C:19]([C:21]([O:23]CC)=[O:22])[N:18]=[N:17]2)=[N:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[OH-].[Li+].Cl>O>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([N:16]2[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[N:18]=[N:17]2)=[N:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68494694HCID 68494694, compound

Product 1

HCID 68492838HCID 68492838, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 1-(5-(benzylcarbamoyl)-4-methylthiazol-2-yl)-1H-1,2,3-triazole-4-carboxylate (0.20 g, 0.54 mmol) in a 1:1 mixture of tetrahydrofuran:water (20 mL) was added lithium hydroxide (0.11 g, 2.69 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, acidified with 10% HCl solution and extracted with dichloromethane (2×50 mL). The organic layer was separated, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to afford the title compound as a white solid in 53% yield (0.27 g): 1H NMR (300 MHz, DMSO-d6) δ 9.15 (s, 1H), 9.03 (t, J=6.0 Hz, 1H), 7.35-7.22 (m, 5H), 4.46 (d, J=6.0 Hz, 2H), 2.63 (s, 3H); MS (ES+) m/z 344.3 (M+1).

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  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-3d643a97934c4216b776d4e8eacf7d74
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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