Imidazole → HCID 19045652, compound

HRID 1781502Notes

Reaction equation

HRID 1781502 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.[C:27]([CH2:29][C:30]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:31][CH2:32][CH2:33]O)#[N:28]>C(Cl)Cl>[C:35]1([C:30]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([CH2:31][CH2:32][CH2:33][I:25])[CH2:29][C:27]#[N:28])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 19045637HCID 19045637, compound

Product 1

HCID 19045652HCID 19045652, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of triphenylphosphine (1.68 g) in methylene chloride (30 ml) and imidazole (0.44 g) was added iodine (1.62 g). To this mixture was added a solution of 5-cyano-4,4-diphenylpentanol (1.3 g) in methylene chloride (5 ml) dropwise. After completion of dropwise addition, the mixture was stirred at room temperature overnight. The reaction mixture was washed with a saturated aqueous solution of sodium thiosulfate, dried over anhydrous sodium sulfate, and concentrated to dryness. To the group was added isopropyl ether, and the insoluble matter was filtered off. The filtrate was concentrated to dryness to provide the title compound (1.5 g) as colorless syrup.

Workup

  1. additionAfter completion of dropwise addition
  2. washThe reaction mixture was washed with a saturated aqueous solution of sodium thiosulfate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated to dryness
  5. additionTo the group was added isopropyl ether
  6. filtrationthe insoluble matter was filtered off
  7. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-c3f6e8f485644f5ca4e7f158571808af
Source dataset
uspto-grants-1997_05
Patent number
US05633248

Reaction notes

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