Water → HCID 12993710, compound

HRID 1168135Notes

Reaction equation

HRID 1168135 reaction equation
[Cl:1][C:2]1[C:11]([N:12]2[C:16](=[O:17])[NH:15][N:14]=[N:13]2)=[C:10]([Cl:18])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CI.[C:21](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:1][C:2]1[C:11]([N:12]2[C:16](=[O:17])[N:15]([CH3:21])[N:14]=[N:13]2)=[C:10]([Cl:18])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

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-6ef29beecab84d6aaa641b169f648490
Source dataset
uspto-grants-2003_09
Patent number
US06624121B1

Reaction notes

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