Lithium Hydroxide → HCID 24959696, compound

HRID 2381853Notes

Reaction equation

HRID 2381853 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[N:11]=[N:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:8]2)[S:4][C:3]=1[C:18]([O:20]CC)=[O:19].O1CCCC1.[OH-].[Li+]>O>[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[N:11]=[N:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:8]2)[S:4][C:3]=1[C:18]([OH:20])=[O:19]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 24959335HCID 24959335, compound

Product 1

HCID 24959696HCID 24959696, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 3-methyl-5-(5-phenyl-2H-tetrazol-2-yl)thiophene-2-carboxylate (0.16 g, 0.51 mmol) in a 1:1 mixture of tetrahydrofuran:water (10 mL) was added lithium hydroxide (0.11 g, 2.55 mmol). The reaction mixture was refluxed for 18 hours and allowed to cool to ambient temperature. The organic solvent was removed in vacuo. The aqueous solution was acidified with 10% aqueous solution. The white solid was collected by filtration, washed with water and dried to afford the title compound as red colored solid (0.12 g, 82%): 1H NMR (300 MHz, DMSO-d6) δ 8.14-8.11 (m, 2H), 7.75 (s, 1H), 7.62-7.60 (m, 3H), 2.54 (s, 3H); MS (ES+) m/z 287.2 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. customThe organic solvent was removed in vacuo
  3. filtrationThe white solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b687c5d01b56436ea56ff8b1219cb8a3
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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