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

HRID 905338Notes

Reaction equation

HRID 905338 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-trifluorometylphenoxy)-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 C26H30ClF3H2O5 : 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-c06b33d77ae0404f9d7a3503f481ca16
Source dataset
uspto-grants-1983_12
Patent number
US04422868

Reaction notes

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