Acetic Acid → 4-[(acetyloxy)methyl]-1,3-dihydro-5-(4-methoxybenzoyl)-2H-imidazol-2-one

HRID 370553

Reaction equation

HRID 370553 reaction equation
Br[CH2:2][C:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]=1[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.[C:19]([OH:22])(=[O:21])[CH3:20]>C([O-])(=O)C.[Ag+].[Ag]Br>[C:19]([O:22][CH2:2][C:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]=1[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 128560344-(bromomethyl)-1,3-dihydro-5-(4-methoxybenzoyl)-2H-imidazol-2-one

Product 1

HCID 134772254-[(acetyloxy)methyl]-1,3-dihydro-5-(4-methoxybenzoyl)-2H-imidazol-2-one

Reagents, catalysts & solvents 2

HCID 11246Silver acetateCatalystHCID 66199Silver bromideCatalyst

Conditions

Temperature
25 °C

Procedure

5-(Bromomethyl)-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one (3.1 g) is dissolved in 80 ml of acetic acid by warming on a steam bath. The solution obtained is allowed to cool to about 25°-45° C. and 1.7 g of silver acetate is added. The mixture is stirred at 25° C. for 16 hours and the precipitate which forms (silver bromide) is removed by filtration. The filtrate is concentrated to about 10 ml and a solid crystallizes. This is separated by filtration and recrystallized from acetic acid to give 4-[(acetyloxy)methyl]-1,3-dihydro-5-(4-methoxybenzoyl)-2H-imidazol-2-one melting at about 155°-162° C. This compound has the following structural formula: ##STR7##

Workup

  1. temperatureby warming on a steam bath
  2. customThe solution obtained
  3. temperatureto cool to about 25°-45° C.
  4. customis removed by filtration
  5. concentrationThe filtrate is concentrated to about 10 ml
  6. customa solid crystallizes
  7. customThis is separated by filtration
  8. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-b352a1b7a6e44e7789fb391720e00d48
Source dataset
uspto-grants-1985_07
Patent number
US04526981

Linked notes

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