Hydrochloric Acid → HCID 66654004, compound

HRID 517698Notes

Reaction equation

HRID 517698 reaction equation
C([O:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]=[N:8][N:7]=1)(=O)C.[OH-].[Li+].Cl>O.CO.O1CCCC1>[OH:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[N:9]=[N:8][N:7]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66654534HCID 66654534, compound2×

Product 1

HCID 66654004HCID 66654004, compoundYield 69.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of [1-(4-cyanophenyl)-1H-tetrazol-5-yl]methyl acetate (2.48 g, 10.2 mmol, Intermediate 8) in water (15 mL), methanol (15 mL) and tetrahydrofuran (THF) (30 mL), cooled in an ice bath, was added lithium hydroxide (0.244 g, 10.2 mmol). The reaction mixture was stirred at 0-5° C. for 1.5 hours. The reaction mixture was acidified with the addition of 2N HCl (5.5 ml). The majority of the organic solvent was then removed from the reaction mixture under vacuum leading to precipitation of a white solid which was filtered then dried under vacuum at 40° C. for 18 hours to yield the title compound as a white solid (1.43 g)

Workup

  1. customThe majority of the organic solvent was then removed from the reaction mixture under vacuum
  2. customleading to precipitation of a white solid which
  3. filtrationwas filtered
  4. customthen dried under vacuum at 40° C. for 18 hours

Sources & evidence

ORD record
ord-68fe248198e2427781fab812f7640684
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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