Methyl iodide → HCID 13825453, compound

HRID 1389000Notes

Reaction equation

HRID 1389000 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][CH2:10][C:11]1[O:12][C:13]([SH:16])=[N:14][N:15]=1.[OH-].[Na+].I[CH3:20]>O.ClCCl>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][CH2:10][C:11]1[O:12][C:13]([S:16][CH3:20])=[N:14][N:15]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178424799HCID 178424799, compound

Product 1

HCID 13825453HCID 13825453, compoundYield 51.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred mixture of 16.2 g (0.0688 mol) 2-(2,6-dimethylphenylaminomethyl)-5-mercapto-1,3,4-oxadiazole in 200 ml water and 200 ml dichloromethane was added quickly 2.8 g (0.0688 mol) sodium hydroxide. To the resulting reaction mixture was then added 9.9 g (0.0688 mol) iodomethane. The reaction mixture was stirred at about 25° C. for 1 hour and then heated under reflux for 1 hour. After the reaction mixture was allowed to stand overnight at 25° C., the organic layer was separated, dried over magnesium sulfate, filtered and evaporated under reduced pressure to give a yellow solid. Trituration with ethyl ether/petroleum ether gave 8.8 g of 2-(2,6-dimethylphenylaminomethyl)-5-methylthio-1,3,4-oxadiazole, m.p. 84°-85° C. The product is tabulated in Table I as Compound No. 24-A.

Workup

  1. customTo the resulting reaction mixture
  2. temperatureheated
  3. temperatureunder reflux for 1 hour
  4. waitto stand overnight at 25° C.
  5. customthe organic layer was separated
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give a yellow solid

Sources & evidence

ORD record
ord-6b6da7208f4b493d90382568efc592c4
Source dataset
uspto-grants-1981_01
Patent number
US04243408

Reaction notes

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