Water → HCID 14852417, compound

HRID 1762566Notes

Reaction equation

HRID 1762566 reaction equation
[Cl:1][C:2]1[NH:3][C:4]([Cl:25])=[C:5]([Cl:24])[C:6]=1[C:7](=[O:23])[C:8]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([OH:18])=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=1.[H-].[Na+].[CH3:28]I.O>CN(C=O)C>[CH3:28][N:3]1[C:4]([Cl:25])=[C:5]([Cl:24])[C:6]([C:7](=[O:23])[C:8]2[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([OH:18])=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=2)=[C:2]1[Cl:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14852419HCID 14852419, compound

Product 1

HCID 14852417HCID 14852417, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4,5-Trichloro-3-(3,5-di-t-butyl-4-hydroxybenzoyl)pyrrole (3.3 g) dissolved in DMF (35 ml) was treated with sodium hydride (50%, 0.432 g) in 4 portions, under nitrogen with stirring at room temperature. After 1 hour at room temperature, 0.56 ml of methyl iodide was added, dropwise, via microsyringe. After stirring 5 minutes more, the reaction mixture was poured into water (300 ml). The organic layer was separated, dried and evaporated to dryness. The residue was purified on silica gel, eluting with hexane:ethyl acetate (80:20). The pure product was recrystallized from ether-pentane to give 2.73 g of the title compound (mp 155°-156° C.).

Workup

  1. stirringAfter stirring 5 minutes more
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was purified on silica gel
  6. washeluting with hexane:ethyl acetate (80:20)
  7. customThe pure product was recrystallized from ether-pentane

Sources & evidence

ORD record
ord-77c4fdd6a7eb4ca9827d898ceac44815
Source dataset
uspto-grants-1989_05
Patent number
US04833155

Reaction notes

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