Imidazole → HCID 68451982, compound

HRID 2355296Notes

Reaction equation

HRID 2355296 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:25]I.O[CH2:28][C:29]1[CH:44]=[CH:43][C:32]([CH2:33][NH:34][C:35]([C:37]2[N:38]=[CH:39][N:40]([CH3:42])[CH:41]=2)=[O:36])=[CH:31][CH:30]=1>ClCCl>[I:25][CH2:28][C:29]1[CH:44]=[CH:43][C:32]([CH2:33][NH:34][C:35]([C:37]2[N:38]=[CH:39][N:40]([CH3:42])[CH:41]=2)=[O:36])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 59153166HCID 59153166, compound

Product 1

HCID 68451982HCID 68451982, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Gently stir for 30 min a mixture of polymer supported triphenylphosphine (1.0 g, 3 mmol/g, 3.0 mmol), 1H-imidazole (208 mg, 3.06 mmol), and iodine (776 mg; 3.06 mmol) in anhydrous dichloromethane (12 mL). To the reaction mixture, add a mixture of N-(4-(hydroxymethyl)benzyl)-1-methyl-1H-imidazole-4-carboxamide (500 mg, 2.04 mmol) in anhydrous dichloromethane (5.0 mL). Gently stir the reaction mixture for 5 hrs at room temperature. Filter the reaction mixture and wash the filtrate with an aqueous 10% sodium thiosulfate solution. Separate the aqueous layer. Wash the organic layer with water, dry over magnesium sulfate, and concentrate to the title compound (532 mg, 1.50 mmol). MS (m/z): 356 (M+1).

Workup

  1. additiona mixture of polymer
  2. additionTo the reaction mixture, add
  3. stirringGently stir the reaction mixture for 5 hrs at room temperature
  4. filtrationFilter the reaction mixture
  5. washwash the filtrate with an aqueous 10% sodium thiosulfate solution
  6. customSeparate the aqueous layer
  7. washWash the organic layer with water
  8. dry with materialdry over magnesium sulfate

Sources & evidence

ORD record
ord-52c6591d067e477fbb36f4436804ce5c
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

Loading…