Imidazole → HCID 135725039, compound

HRID 1369952Notes

Reaction equation

HRID 1369952 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.[C:22]([C:26]1[CH:27]=[C:28]([C:37]2[O:38][CH:39]=[C:40]([CH2:42][CH2:43]O)[N:41]=2)[CH:29]=[C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:31]=1[OH:32])([CH3:25])([CH3:24])[CH3:23].N1C=CN=C1>C(Cl)Cl>[C:22]([C:26]1[CH:27]=[C:28]([C:37]2[O:38][CH:39]=[C:40]([CH2:42][CH2:43][I:20])[N:41]=2)[CH:29]=[C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:31]=1[OH:32])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 135509425HCID 135509425, compound

Product 1

HCID 135725039HCID 135725039, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphenylphosphine (118.8 mmole, 31.12 g), in methylene chloride (460 ml) was treated with iodine (approximately 30.17 g) until a dull yellow color persisted. The reaction stirred fifteen minutes, then a solution of 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-4-(2-hydroxyethyl)oxazole (79.2 mmole, 25.10 g) and imidazole (158.3 g, 10.77 g) in methylene chloride (300 ml) was added over a ten minute period. At 3.0 hours the reaction was concentrated in vacuo then taken up into methylene chloride and subjected to flash silica gel filtration. Desired product was eluted with 1:1 ethyl acetate:hexane, collecting 500 ml tractions. Desired fractions were combined, washed with 1×250 ml 1N sodium thiosulfate and 1×250 ml brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 32.53 g (96%) of the title compound.

Workup

  1. concentrationAt 3.0 hours the reaction was concentrated in vacuo
  2. filtrationsubjected to flash silica gel filtration
  3. washDesired product was eluted with 1:1 ethyl acetate
  4. customhexane, collecting 500 ml tractions
  5. washwashed with 1×250 ml 1N sodium thiosulfate and 1×250 ml brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbdb467ce6134401a119b67524561f5d
Source dataset
uspto-grants-2003_06
Patent number
US06579871B2

Reaction notes

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