Triethylamine → Flutolanil

HRID 839041Notes

Reaction equation

HRID 839041 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>O1CCCC1>[CH3:2][CH:1]([O:4][C:5]1[CH:6]=[C:7]([NH:8][C:23]([C:22]2[C:21]([C:20]([F:19])([F:30])[F:31])=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[CH:9]=[CH:10][CH:11]=1)[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 5732203-(Propan-2-yloxy)aniline

Product 1

HCID 47898FlutolanilYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution containing 1.5 g (0.01 mole) of m-isopropoxyaniline and 1.2 g (0.011 mole) of triethylamine, while being cooled in ice water, was added slowly 2.3 g (0.011 mole) of o-trifluoromethylbenzoyl chloride. After having been stirred for 2 hours at room temperature, the reaction mixture was freed from triethylamine hydrochloride by filtration and then from the solvent by distillation under reduced pressure. The residue was recrystallized from n-hexane to obtain 2.9 g (91% yield) of the intended product melting at 95° to 97° C.

Workup

  1. filtrationthe reaction mixture was freed from triethylamine hydrochloride by filtration
  2. distillationfrom the solvent by distillation under reduced pressure
  3. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-4f116d2198b148e8ad29c69f17b767cf
Source dataset
uspto-grants-1978_06
Patent number
US04093743

Reaction notes

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