Methyl iodide → HCID 13173184, compound

HRID 980360Notes

Reaction equation

HRID 980360 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[S:24][C:25]#N)[CH2:21][CH2:20][S:19]3)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].CI.[OH-].[K+]>CO.O>[C:12]([C:9]1[CH:8]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[S:24][CH3:25])[CH2:21][CH2:20][S:19]3)[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:13])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 13173180HCID 13173180, compound

Product 1

HCID 13173184HCID 13173184, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In 10 ml of methanol was dissolved 1.3 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-thiocyanato-2,3-dihydroimidazo[2,1-b]thiazole and after cooling the solution to 0° C., 0.65 g of methyl iodide was added dropwise to the solution with stirring and further a solution of 0.2 g of potassium hydroxide dissolved in a mixture of 2 ml of water and 2 ml of methanol was added dropwise to the solution. After 30 minutes, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography using chloroform as the eluent and further recrystallized from ethanol to provide 0.18 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-methylthio-2,3-dihydroimidazo[2,1-b]thiazole.

Workup

  1. additionwas added dropwise to the solution
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography
  4. customfurther recrystallized from ethanol

Sources & evidence

ORD record
ord-4cfc2a3ab69a4605b7e1d48fee9bbc1f
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

Loading…