Methyl iodide → HCID 178503859, compound

HRID 1461769Notes

Reaction equation

HRID 1461769 reaction equation
[CH3:1]I.[C:3]([NH:7][C:8]([NH:10][C:11]1[C:12]([CH:28]([CH3:30])[CH3:29])=[N:13][C:14]([O:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:15][C:16]=1[CH:17]([CH3:19])[CH3:18])=[S:9])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:3]([NH:7][C:8](=[N:10][C:11]1[C:12]([CH:28]([CH3:30])[CH3:29])=[N:13][C:14]([O:20][C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)=[CH:15][C:16]=1[CH:17]([CH3:19])[CH3:18])[S:9][CH3:1])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 19979380HCID 19979380, compound

Product 1

HCID 178503859HCID 178503859, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.0 g of methyl iodide are added at room temperature to 2.50 g of 1-tert.-butyl-3-[2,4-diisopropyl-6-(4-chlorophenoxy)-pyrid-3-yl]-thiourea in 30 ml of ethanol and the mixture is heated at +75° C. for 5 hours. The mixture is then concentrated by evaporation and the residue is taken up in methylene chloride and washed twice with dilute sodium bicarbonate solution. The organic phase is dried over magnesium sulfate and the solvent is evaporated. The crude product is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 1:3). 1-tert.-Butyl-3-[2,4-diisopropyl-6-(4-chlorophenoxy)-pyrid-3-yl]-S-methyl-isothiourea is obtained in the form of a colourless crystalline powder, m.p. 95°-100° C.

Workup

  1. temperaturethe mixture is heated at +75° C. for 5 hours
  2. concentrationThe mixture is then concentrated by evaporation
  3. washwashed twice with dilute sodium bicarbonate solution
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. customthe solvent is evaporated
  6. customThe crude product is purified by column chromatography on silica gel (eluant: ethyl acetate/hexane 1:3)

Sources & evidence

ORD record
ord-2c68b41c8771442a9b69661ddf239209
Source dataset
uspto-grants-1991_12
Patent number
US05077304

Reaction notes

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