Sodium Hydroxide → 4,5-Dichloro-6-(1-methyl-5-pyrazolylcarbonyl)-1,3-benzodioxole-2-carboxylic acid

HRID 1089163Notes

Reaction equation

HRID 1089163 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:12]2[O:11][CH:10]([C:13]([O:15]CC)=[O:14])[O:9][C:8]=2[CH:7]=[C:6]([C:18]([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=2)=[O:19])[C:5]=1[Cl:26]>O.C(O)C>[Cl:3][C:4]1[C:12]2[O:11][CH:10]([C:13]([OH:15])=[O:14])[O:9][C:8]=2[CH:7]=[C:6]([C:18]([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=2)=[O:19])[C:5]=1[Cl:26]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 14748603Ethyl 4,5-dichloro-6-(1-methyl-5-pyrazolylcarbonyl)-1,3-benzodioxole-2-carboxylate

Product 1

HCID 147486184,5-Dichloro-6-(1-methyl-5-pyrazolylcarbonyl)-1,3-benzodioxole-2-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.36 g of sodium hydroxide in 15 ml of water is added to a suspension of 1.86 g of ethyl 4,5-dichloro-6-(1-methyl-5-pyrazolylcarbonyl)-1,3-benzodi oxole-2-carboxylate in 35 ml of ethanol and the mixture is stirred at room temperature for 0.5 hour. The reaction mixture is concentrated to remove ethanol and adjusted to pH 1 with aqueous 10% hydrochloric acid. The resultant crystals are collected by filtration, washed successively with water and isopropyl ether and dried to give 1.66 g of 4,5-dichloro-6-(1-methyl-5-pyrazolylcarbonyl)-1,3-benzodioxole-2-carboxylic acid. Yield: 97%

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customto remove ethanol
  3. filtrationThe resultant crystals are collected by filtration
  4. washwashed successively with water and isopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-544a69d79fc5422ab23f742a833927e2
Source dataset
uspto-grants-1990_10
Patent number
US04965282

Reaction notes

Loading…