Water → HCID 12993710, compound

HRID 586120Notes

Reaction equation

HRID 586120 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([N:11]2[C:15](=[O:16])[NH:14][N:13]=[N:12]2)[C:5]=1[Cl:17].CI.[C:21](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:17][C:5]1[C:6]([N:11]2[C:15](=[O:16])[N:14]([CH3:21])[N:13]=[N:12]2)=[C:7]([Cl:10])[CH:8]=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135553025HCID 135553025, compound

Product 1

HCID 12993710HCID 12993710, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Methyl-2,4-dichloro-3-(4,5-dihydro-5-oxo-1H-tetrazol-1-yl)benzoate (4.00 g), methyl iodide (2.36 g) and potassium carbonate (2.29 g) were suspended in N,N-dimethylformamide (30 ml) and stirred at 60° C. After reaction, cold water was added to the reaction mixture and the mixture was extracted with ethyl acetate (150 ml) and dried with anhydrous magnesium sulfate. By distilling off the ethyl acetate, the objective methyl 2,4-dichloro-3-(4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl)benzoate (4.13 g, yield 98%) was obtained. mp: 135-137° C.

Workup

  1. additionwas added to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate (150 ml)
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationBy distilling off the ethyl acetate

Sources & evidence

ORD record
ord-9b26f25000764cb4ab66b1348ab18822
Source dataset
uspto-grants-2005_08
Patent number
US06936570B2

Reaction notes

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