Iodine → HCID 57772063, compound

HRID 1661918Notes

Reaction equation

HRID 1661918 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:33][CH3:34])=[CH:20][C:21]([CH:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[S:31][CH3:32])O)=[CH:22][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].II.[PH2](=O)O.C(OCC)(=O)C>C(O)(=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:13]3[C:19]([O:33][CH3:34])=[CH:20][C:21]([CH2:23][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[S:31][CH3:32])=[CH:22][C:12]=3[N:11]=2)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 807IodineHCID 8857Ethyl AcetateHCID 4124402Phosphinic AcidHCID 57772034HCID 57772034, compound

Product 1

HCID 57772063HCID 57772063, compoundYield 118.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 797 mg (1.67 mmol) [2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-(2-methylsulfanyl-phenyl)-methanol, 436 mg iodine in 13 ml acetic acid (100%), 0.88 ml of phosphinic acid (ca. 5 equiv.) is added at room temperature. The mixture is heated to 60° C. and stirred for 1 h. After that the reaction mixture is allowed to cool to room temperature and 100 ml ethyl acetate is added. The combined organic layers are washed with 4N NaOH-solution (4×), water (2×) and brine, dried over MgSO4, filtered and the filtrate is concentrated in vacuo to afford 914 mg of the title compound as a colorless oil.

Workup

  1. additionis added at room temperature
  2. temperatureto cool to room temperature
  3. washThe combined organic layers are washed with 4N NaOH-solution (4×), water (2×) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-a77407bede874696aff880bca510083c
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

Loading…