Iodine → HCID 11269925, compound

HRID 1794585Notes

Reaction equation

HRID 1794585 reaction equation
[CH2:1]([O:3][C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[C:6]([NH:8][N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]1[CH2:15][CH2:16][CH3:17])=[O:7])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[I:28]I.C(OCC)(=O)C>O1CCOCC1.O>[CH2:1]([O:3][C:4]1[CH:21]=[CH:20][CH:19]=[CH:18][C:5]=1[C:6]([NH:8][N:9]1[C:13]([I:28])=[C:12]([CH3:14])[N:11]=[C:10]1[CH2:15][CH2:16][CH3:17])=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 11414984HCID 11414984, compound

Product 1

HCID 11269925HCID 11269925, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

2-Ethoxy-N-(4-methyl-2-propylimidazol-1-yl)benzamide from Example D (3.5 g, 12.2 mmol) is dissolved in 480 ml of a dioxane/water mixture, and sodium carbonate (3.9 g, 36.6 mmol) and iodine (6.8 g, 26.8 mmol) are added. The mixture is stirred with exclusion of light at room temperature for 24 hours. 50 ml of ethyl acetate are added to the reaction mixture and washed twice with 50 ml of saturated sodium sulphite solution each time. The combined aqueous phases are re-extracted twice with 50 ml of ethyl acetate each time, and the combined organic phase is dried with sodium sulphate and concentrated in a rotary evaporator.

Workup

  1. washwashed twice with 50 ml of saturated sodium sulphite solution each time
  2. extractionThe combined aqueous phases are re-extracted twice with 50 ml of ethyl acetate each time
  3. dry with materialthe combined organic phase is dried with sodium sulphate
  4. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-03b5f1f71f14405ab2e62bda00dbf183
Source dataset
uspto-grants-2006_04
Patent number
US07022847B2

Reaction notes

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