Methyl iodide → 2,6-dichloro-3-methyl-N-[2-[5-(methylthio)-1,3,4-oxadiazol-2-yl]phenyl]benzenamine

HRID 2211185Notes

Reaction equation

HRID 2211185 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:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[O:21][C:20](=[S:22])[NH:19][N:18]=1.[OH-].[Na+].I[CH3:26]>CO>[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:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]1[O:21][C:20]([S:22][CH3:26])=[N:19][N:18]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 99284195-[2-(2,6-Dichloro-3-methyl-phenylamino)-phenyl]-[1,3,4]oxadiazole-2-thiol

Product 1

HCID 193757012,6-dichloro-3-methyl-N-[2-[5-(methylthio)-1,3,4-oxadiazol-2-yl]phenyl]benzenamineYield 86.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a room temperature suspension of 5-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]-1,3,4-oxadiazole-2(3H)-thione (1.706 g, 4.85 mmoles) in 70 ml of methanol is added dropwise 5.0 ml of 1.0N sodium hydroxide. The clear pale yellow solution is stirred at room temperature for 10 minutes. Iodomethane (320.0 μl, 5.13 mmoles) is added dropwise, and stirring is continued for six hours. The white solid is collected by filtration and dried in vacuo overnight at 60° C. to provide 1.530 g (86%) of 2,6-dichloro-3-methyl-N-[2-[5-(methylthio)-1,3,4-oxadiazol-2-yl]phenyl]benzenamine, mp 170°-171° C.

Workup

  1. stirringstirring
  2. waitis continued for six hours
  3. filtrationThe white solid is collected by filtration
  4. customdried in vacuo overnight at 60° C.

Sources & evidence

ORD record
ord-9c366ee8bb21425f82de0c3bb8529208
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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