Pyridine → N-Benzyl-2-[4-chloro-3-(trifluoromethyl)phenoxy]butanamide

HRID 580432Notes

Reaction equation

HRID 580432 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[Cl:15][C:16]1[CH:28]=[CH:27][C:19]([O:20][CH:21]([CH2:25][CH3:26])[C:22](Cl)=[O:23])=[CH:18][C:17]=1[C:29]([F:32])([F:31])[F:30]>C1(C)C=CC=CC=1>[CH2:1]([NH:8][C:22](=[O:23])[CH:21]([O:20][C:19]1[CH:27]=[CH:28][C:16]([Cl:15])=[C:17]([C:29]([F:31])([F:32])[F:30])[CH:18]=1)[CH2:25][CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7504BenzylamineHCID 20133796HCID 20133796, compound

Product 1

HCID 13342492N-Benzyl-2-[4-chloro-3-(trifluoromethyl)phenoxy]butanamideYield 43%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

In 50 ml of toluene were dissolved 1.6 g (0.015 mole) of benzylamine and 2.4 g (0.030 mole) of pyridine. Then, was added dropwise thereto a solution of 3.0 g (0.010 mole) of 2-(4-chloro-3-trifluoromethylphenoxy)-butyroyl chloride in 30 ml of toluene and the mixture was treated, according to the same procedure as in Synthesis Example 10. The resultant crude crystals were recrystallized from ethanol to give 1.6 g of N-benzyl-2-(4-chloro-3-trifluoromethylphenoxy)-butyramide melting at 93°-95° C. as colorless needless.

Workup

  1. additionThen, was added dropwise
  2. customaccording to the same procedure as in Synthesis Example 10
  3. customThe resultant crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-115e5a1432d94a2e9860f9bcd871ae00
Source dataset
uspto-grants-1988_06
Patent number
US04753674

Reaction notes

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