Acetonitrile → HCID 12926725, compound

HRID 478079Notes

Reaction equation

HRID 478079 reaction equation
[Cl-].[CH2:2]([O:4][C:5](=[O:8])[CH2:6][NH2:7])[CH3:3].[N+:9]([C:12]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:31])[F:30])=[CH:24][C:23]=2[Cl:33])=[CH:17][C:13]=1[C:14](Cl)=[O:15])([O-:11])=[O:10].C(#N)C.[OH-].[Na+]>O>[CH2:2]([O:4][C:5]([CH2:6][NH:7][C:14](=[O:15])[C:13]1[CH:17]=[C:18]([O:21][C:22]2[C:27]([Cl:28])=[CH:26][C:25]([C:29]([F:32])([F:30])[F:31])=[CH:24][C:23]=2[Cl:33])[CH:19]=[CH:20][C:12]=1[N+:9]([O-:11])=[O:10])=[O:8])[CH3:3]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 129267235-[2,6-Dichloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoyl chlorideHCID 24180951HCID 24180951, compound

Product 1

HCID 12926725HCID 12926725, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7 g of aminoacetic acid ethyl ester chloride, 20.7 g of 2-nitro-5-(2,6-dichloro-4-trifluoromethyl-phenoxy)-benzoic acid chloride and 180 ml of acetonitrile were initially introduced into the reaction vessel. 4 g of sodium hydroxide, dissolved in 10 ml of water, were added dropwise at -10° to -5° C. The reaction mixture was then poured onto water and adjusted to pH 10 and the crystalline product was filtered off. 23 g (95% of theory) of 5-(2,6-dichoro-4-trifluoromethyl-phenoxy)-2-nitro-benzoic acid (ethoxycarbonylmethyl)-amide with a melting point of 146° C. were obtained.

Workup

  1. additionwere added dropwise at -10° to -5° C
  2. additionThe reaction mixture was then poured onto water
  3. filtrationthe crystalline product was filtered off

Sources & evidence

ORD record
ord-1acdb8b126534fa1bf4c80aef85d6ca3
Source dataset
uspto-grants-1989_12
Patent number
US04889946

Reaction notes

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