Water → HCID 178521961, compound

HRID 1930741Notes

Reaction equation

HRID 1930741 reaction equation
[O:1]([CH2:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:27]=[CH:26][C:17]([O:18][C:19]3[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=3)=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1([N:34]=[C:35]=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O.C(OCC)(=O)C>CN(C)C=O>[O:1]([CH2:8][C:9]1[NH:10][CH:11]=[C:12]([C:14]2[CH:27]=[CH:26][C:17]([O:18][C:19]3[CH:20]=[CH:21][C:22]([NH:23][C:35]([NH:34][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[O:36])=[CH:24][CH:25]=3)=[CH:16][CH:15]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 8857Ethyl AcetateHCID 178507748HCID 178507748, compound

Product 1

HCID 178521961HCID 178521961, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture containing 4-{4-[2-(phenoxymethyl)-1H-imidazol-4-yl]phenoxy}aniline (0.2 g, 0.56 mmol) and phenylisocyanate (0.136 g, 1.12 mmol) in 3 ml of dimethylformamide is heated at 100° C. for two hours. After returning to ambient temperature 20 ml of water and 30 ml of ethyl acetate are added followed by extraction, then the organic phase is washed with a saturated sodium chloride solution. The organic phase is dried over sodium sulfate, filtered and concentrated to dryness under vacuum. The solid obtained is purified on a silica column (eluent: dichloromethane-ethanol-ammonia 96-2-2) in order to obtain a white-coloured powder with a yield of 21%.

Workup

  1. customAfter returning to ambient temperature
  2. additionare added
  3. extractionfollowed by extraction
  4. washthe organic phase is washed with a saturated sodium chloride solution
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under vacuum
  8. customThe solid obtained
  9. customis purified on a silica column (eluent: dichloromethane-ethanol-ammonia 96-2-2) in order
  10. customto obtain a white-coloured powder with a yield of 21%

Sources & evidence

ORD record
ord-0388aee523cf4d228ab4e6f78b4c0636
Source dataset
uspto-grants-2012_05
Patent number
US08188133B2

Reaction notes

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