Hydrochloric Acid → 4-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzoic acid

HRID 2047477Notes

Reaction equation

HRID 2047477 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[N:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][CH:9]=2)[N:6]=[N:5][N:4]=1.[OH-].[Li+].Cl>C1COCC1.CO.O>[F:19][C:2]([F:1])([F:18])[C:3]1[N:7]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([OH:14])=[O:13])=[CH:10][CH:9]=2)[N:6]=[N:5][N:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67233109HCID 67233109, compound

Product 1

HCID 672325714-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzoic acidYield 87.2%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of the compound (5.2 g) obtained in step 1 in THF/methanol/water (6.0/18/9.5 mL) was added 4N aqueous lithium hydroxide solution (9.5 mL), and the mixture was stirred at room temperature for 4 hr. The mixture was acidified with 1N hydrochloric acid, concentrated under reduced pressure, diluted with water, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried, filtered through silica gel (eluted with ethyl acetate). The filtrate was concentrated under reduced pressure, and crystallized from ethyl acetate/hexane to give the title compound (4.3 g, 86%) as a pale-yellow powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. customdried
  6. filtrationfiltered through silica gel (eluted with ethyl acetate)
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-51c27715abe843d6a77452ea9472847f
Source dataset
uspto-grants-2013_11
Patent number
US08592454B2

Reaction notes

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