Methyl iodide → HCID 14852422, compound

HRID 2107742Notes

Reaction equation

HRID 2107742 reaction equation
[CH3:1][S:2][C:3]1[NH:4][CH:5]=[C:6]([C:8](=[O:24])[C:9]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([OH:19])=[C:11]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=2)[CH:7]=1.[H-].[Na+].[CH3:27]I>CN(C)C=O>[CH3:27][N:4]1[CH:5]=[C:6]([C:8](=[O:24])[C:9]2[CH:14]=[C:13]([C:15]([CH3:16])([CH3:17])[CH3:18])[C:12]([OH:19])=[C:11]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=2)[CH:7]=[C:3]1[S:2][CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23046301HCID 23046301, compound

Product 1

HCID 14852422HCID 14852422, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2-Methylthio-4-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole (1 g) was added to a cooled, stirred suspension of 0.28 g of sodium hydride (50% in mineral oil) in 20 ml of anhydrous dimethylformamide under nitrogen. After 45 minutes at room temperature, the mixture was cooled to 0° C. and 0.25 ml of methyl iodide was added. After 30 minutes, the reaction mixture was poured into a 10% HCl-ice-water mixture, then extracted three times with 100 ml ethyl acetate. The organic layer was washed five times with 100 ml water, dried and evaporated to dryness. Crystallization of the residue from ethyl acetate-hexane gave 0.93 g of the title compound (mp 173°-175° C.).

Workup

  1. waitAfter 30 minutes
  2. extractionextracted three times with 100 ml ethyl acetate
  3. washThe organic layer was washed five times with 100 ml water
  4. customdried
  5. customevaporated to dryness
  6. customCrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e7ffef75693f49bc8d316c29283ef975
Source dataset
uspto-grants-1990_06
Patent number
US04935440

Reaction notes

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