Acifluorfen → t-Octylammonium 5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate

HRID 1065722

Reaction equation

HRID 1065722 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11].[C:25]([NH2:33])([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:26]>C(COC)OC>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([O-:12])=[O:11].[C:25]([NH3+:33])([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 44073AcifluorfenHCID 61017tert-Octylamine

Product 1

HCID 21280025t-Octylammonium 5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoateYield 68.7%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid (3.0 g, 0.0083 mole) is dissolved in glyme (20 ml) and t-octylamine (1.17 g, 0.0091 mole) is added rapidly while stirring. The solvent is removed in vacuo and the residue triturated with petroleum ether (bp 30°-60° C.) and dried to give 2.8 g of product, mp 140°-57° C. Anal. Calcd. for C22H24ClF3N2O5 : C, 53.82; H, 5.33; N, 5.70; Cl, 7.22; F, 11.61. Found: C, 53.50; H, 5.37; N, 6.06; Cl, 6.87; F, 11.10.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue triturated with petroleum ether (bp 30°-60° C.)
  3. customdried

Sources & evidence

ORD record
ord-99696c06ff584d26b9711ac28c497018
Source dataset
uspto-grants-1982_05
Patent number
US04330324

Linked notes

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