Imidazole → HCID 67706583, compound

HRID 1734884Notes

Reaction equation

HRID 1734884 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10]Cl)[C:5]=1[NH:12][C:13](=[O:29])[CH2:14][CH:15]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:22][C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)([CH3:3])[CH3:2].[NH:30]1[CH:34]=[CH:33][N:32]=[CH:31]1.[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][C:31]2[NH:30][CH:34]=[CH:33][N:32]=2)[C:5]=1[NH:12][C:13](=[O:29])[CH2:14][CH:15]1[C:28]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:22][C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 5238Sodium IodideHCID 19966136HCID 19966136, compound

Product 1

HCID 67706583HCID 67706583, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 500 mg (1.23 mmol) of N-(2-isopropyl-6-chloromethylphenyl)-2-(9H-xanthen-9-yl)acetamide [prepared as described in Preparation 28(iv)], 847 mg (12.3 mmol) of imidazole and 277 mg (1.9 mmol) of sodium iodide in 10 ml of N,N-dimethylformamide was stirred at 90° C. for 2 hours and then the temperature was lowered to room temperature. The resulting mixture was diluted with ethyl acetate. The diluted mixture was washed several times with water and once with a saturated aqueous solution of sodium chloride. The organic phase was dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was triturated with a mixture of diethyl ether and hexane, and the resulting crystallized product was collected to give 471 mg (yield 88%) of the title compound as crystals, melting at 193°-195° C. (after recrystallization from a mixture of methanol, diethyl ether and hexane).

Workup

  1. customwas lowered to room temperature
  2. washThe diluted mixture was washed several times with water
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was triturated with a mixture of diethyl ether and hexane
  6. customthe resulting crystallized product
  7. customwas collected

Sources & evidence

ORD record
ord-98b0f37e4b40496fa48b04837730f2b4
Source dataset
uspto-grants-1996_07
Patent number
US05534529

Reaction notes

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