Methyl iodide → HCID 22450431, compound

HRID 249516Notes

Reaction equation

HRID 249516 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][N:7]([CH3:12])[C:8]([NH:10][CH3:11])=[S:9])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:17]I>C1COCC1>[CH3:17][S:9][C:8](=[N:10][CH3:11])[N:7]([CH2:6][C:5]1[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 8785982HCID 8785982, compound

Product 1

HCID 22450431HCID 22450431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 50 ml of dry THF was dissolved 4.69 g (0.0205 mole) of N-(4-chlorobenzyl)-N-methyl-N'-methylthiourea, followed by addition of 0.82 g of 60% sodium hydride (oil). The mixture was refluxed for 1 hour. Then, under cooling with ice-water and stirring, 1.277 ml of methyl iodide was added dropwise and after completion of dropwise addition, the mixture was further stirred at room temperature for 45 minutes. The THF was distilled off and the residue was diluted with water (about 50 ml), saturated with sodium chloride, and extracted with AcOEt (100 ml×3). The extract was dried over MgSO4 and the solvent was distilled off to give 5.11 g of crude S-methyl-N-(4-chlorobenzyl)-N-methyl-N'-methylisothiourea as a colorless-pale yellow oil.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. additionafter completion of dropwise addition
  3. stirringthe mixture was further stirred at room temperature for 45 minutes
  4. distillationThe THF was distilled off
  5. additionthe residue was diluted with water (about 50 ml), saturated with sodium chloride
  6. extractionextracted with AcOEt (100 ml×3)
  7. dry with materialThe extract was dried over MgSO4
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-6633b0d08fed44b094991b009263f568
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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