Imidazole → HCID 44243608, compound

HRID 660781Notes

Reaction equation

HRID 660781 reaction equation
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[C:27]([O:31][C:32](=[O:42])[NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40]O)([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[C:27]([O:31][C:32](=[O:42])[NH:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH2:40][I:25])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 15292992tert-Butyl [2-(hydroxymethyl)phenyl]carbamate

Product 1

HCID 44243608HCID 44243608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of imidazole (404 mg, 5.94 mmol) and triphenylphosphine (1.56 g, 5.94 mmol) in methylene chloride (50 mL) is added iodine (1.51 g, 5.94 mmol) in portions. When the reaction is complete, a solution of (2-hydroxymethylphenyl)-carbamic acid tert-butyl ester (1.2 g, 5.4 mmol) in methylene chloride (20 mL) is added dropwise and the mixture is stirred at RT for 75 min. The mixture is concentrated and the insoluble material is filtered. The filtrate is evaporated and the residue is purified by column chromatography using a gradient of 25-50% MTBE/methylene chloride as eluent to give the title compound.

Workup

  1. concentrationThe mixture is concentrated
  2. filtrationthe insoluble material is filtered
  3. customThe filtrate is evaporated
  4. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-7e8d23d2da1a45d4b826b93f8df18597
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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