HCID 12993710, compound → HCID 11737800, compound

HRID 1168134Notes

Reaction equation

HRID 1168134 reaction equation
[Cl:1][C:2]1[C:11]([N:12]2[C:16](=[O:17])[N:15]([CH3:18])[N:14]=[N:13]2)=[C:10]([Cl:19])[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5]>O1CCOCC1.[OH-].[Na+].O>[Cl:1][C:2]1[C:11]([N:12]2[C:16](=[O:17])[N:15]([CH3:18])[N:14]=[N:13]2)=[C:10]([Cl:19])[CH:9]=[CH:8][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 1

HCID 12993710HCID 12993710, compound

Product 1

HCID 11737800HCID 11737800, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 2,4-dichloro-3-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)benzoate (4.10 g) in dioxane (70 ml), 10N sodium hydroxide (2.0 ml) and water (4 ml) were added and the mixture was stirred at 60° C. for 1.5 hours. After concentrating under reduced pressure and the addition of water (50 ml), an aqueous solution of sodium hydroxide was added and washed with ethyl acetate (150 ml). The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated salt water and dried with anhydrous magnesium sulfate. By distilling off of ethyl acetate, the objective 2,4-dichloro-3-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)benzoic acid (3.42 g, yield 87%) was obtained. mp: 221-225° C.

Workup

  1. concentrationAfter concentrating under reduced pressure
  2. additionthe addition of water (50 ml)
  3. additionan aqueous solution of sodium hydroxide was added
  4. washwashed with ethyl acetate (150 ml)
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated salt water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. distillationBy distilling off of ethyl acetate

Sources & evidence

ORD record
ord-ad8576aade504560a5534d2cd8591cf9
Source dataset
uspto-grants-2003_09
Patent number
US06624121B1

Reaction notes

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