HCID 12993710, compound → HCID 11737800, compound

HRID 1006399Notes

Reaction equation

HRID 1006399 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 (4ml) 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-6dd4f671e5b84914b2e04bf4cc2db35c
Source dataset
uspto-grants-2004_09
Patent number
US06790810B2

Reaction notes

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