Imidazole → HCID 44243608, compound

HRID 1642604Notes

Reaction equation

HRID 1642604 reaction equation
N1C=CN=C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=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 (2.6 g, 37 mmol) and PPh3 (9.6 g, 37 mmol) in DCM (180 mL) is slowly added I2 (9.4 g, 37 mmol) over a period of 10 min. The mixture is stirred at ambient temperature for 30 min. Then a solution of (2-hydroxymethylphenyl)-carbamic acid tert-butyl ester (7.5 g, 33.6 mmol) in DCM (40 mL) is added dropwise. The mixture is stirred at ambient temperature for 1 h, then is concentrated to about 70 mL and the resulting precipitate is filtered and washed with DCM. The filtrate is concentrated and purified to give the title compound as a solid.

Workup

  1. customof 10 min
  2. stirringThe mixture is stirred at ambient temperature for 1 h
  3. concentrationis concentrated to about 70 mL
  4. filtrationthe resulting precipitate is filtered
  5. washwashed with DCM
  6. concentrationThe filtrate is concentrated
  7. custompurified

Sources & evidence

ORD record
ord-a07934c9caaa47d98be08eb13292fe57
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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