Acifluorfen → Dicyclohexylammonium 5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate

HRID 1065721Notes

Reaction equation

HRID 1065721 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(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].[CH:2]1([NH2+:14][CH:8]2[CH2:9][CH2:13][CH2:5][CH2:6][CH2:7]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:3]1

Participants

3

Reactant 1

HCID 44073Acifluorfen

Product 1

HCID 21280067Dicyclohexylammonium 5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoateYield 119.8%

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 dicyclohexylamino (1.64 g, 0.0091 mole) is added at room temperature while stirring. The solvent is removed in vacuo, the residue triturated with petroleum ether (bp 30°-60° C.) and dried to give 2.7 g of product, mp 197°-9° C. Anal. Calcd. for C26H30ClF3N2O5 : C, 57.51; H, 5.56; N, 5.15; Cl, 6.53; F, 10.49. Found C, 57.25; H, 5.71; N, 5.55; Cl, 6.40; F, 10.24.

Workup

  1. additiondicyclohexylamino (1.64 g, 0.0091 mole) is added at room temperature
  2. customThe solvent is removed in vacuo
  3. customthe residue triturated with petroleum ether (bp 30°-60° C.)
  4. customdried

Sources & evidence

ORD record
ord-41a90b58b1914cc588e97bbe38aecef9
Source dataset
uspto-grants-1982_05
Patent number
US04330324

Reaction notes

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