p-Toluenesulfonic acid → 2,6-dichloro-3-methyl-N-[2-(1,3,4-oxadiazol-2-yl)phenyl]benzenamine

HRID 2211184Notes

Reaction equation

HRID 2211184 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH:15][NH2:16])=[O:14].[CH:21](OCC)(OCC)OCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]1[O:14][CH:21]=[N:16][N:15]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 31214Ethyl orthoformateHCID 14951339HCID 14951339, compound

Product 1

HCID 193757002,6-dichloro-3-methyl-N-[2-(1,3,4-oxadiazol-2-yl)phenyl]benzenamineYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a room temperature suspension of 2-[(2,6-dichloro-3-methylphenyl)amino]-benzoic acid hydrazide (355.1 mg, 1.15 mmoles) in 6 ml of ethanol is added 2 ml of triethyl orthoformate followed by p-toluenesulfonic acid (20 mg, 0.11 mmoles). After stirring at room temperature overnight, the clear yellow solution is concentrated in vacuo. The residue is subjected to flash chromatography eluting with hexane:ethyl acetate (3:1). Subsequent recrystallization from ethanol yields 244.1 mg (67%) of 2,6-dichloro-3-methyl-N-[2-(1,3,4-oxadiazol-2-yl)phenyl]benzenamine, mp 180°-181° C.

Workup

  1. concentrationthe clear yellow solution is concentrated in vacuo
  2. washeluting with hexane:ethyl acetate (3:1)
  3. customSubsequent recrystallization from ethanol

Sources & evidence

ORD record
ord-22154f266f6c45058be59d5bc5dab677
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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