Imidazole → HCID 67706583, compound

HRID 977843Notes

Reaction equation

HRID 977843 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-4a47d2962fcc47429402a0cd4d84bd7d
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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