Ammonium Hydroxide → HCID 19032440, compound

HRID 266069Notes

Reaction equation

HRID 266069 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:42]=[CH:41][C:9]([C:10]([CH:12]([N:14]2[CH:18]=[C:17]([CH3:19])[N:16]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][N:29]([C:32]5[CH:37]=[CH:36][C:35]([O:38]C)=[CH:34][CH:33]=5)[CH2:28][CH2:27]4)=[CH:22][CH:21]=3)[C:15]2=[O:40])[CH3:13])=[O:11])=[CH:8][CH:7]=1.[NH4+].[OH-]>ClCCl>[Cl:5][C:6]1[CH:42]=[CH:41][C:9]([C:10]([CH:12]([N:14]2[CH:18]=[C:17]([CH3:19])[N:16]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][N:29]([C:32]5[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=5)[CH2:28][CH2:27]4)=[CH:22][CH:21]=3)[C:15]2=[O:40])[CH3:13])=[O:11])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 19032435HCID 19032435, compound

Product 1

HCID 19032440HCID 19032440, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of 25 g of boron tribromide and 100 ml of dichloromethane was added dropwise a solution of 6.1 g of 1-[1-(4-chlorobenzoyl)ethyl]-1,3-dihydro-3-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-4-methyl-2H-imidazol-2-one in 200 ml of dichloromethane (temp<10° C.). After stirring for 2 hours, the reaction mixture was poured into a mixture of NH4OH and ice. Then there were added 300 ml of dichloromethane and the whole was stirred for 1 hour. The organic layer was separated, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 99:1). The eluent of the desired fraction was evaporated and the residue was triturated in methanol. The product was filtered off and dried, yielding 4.3 g (72.3%) of 1-[1-(4-chlorobenzoyl)ethyl]-1,3-dihydro-3-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-4-methyl-2H-imidazol-2-one; mp. 229.7° C. (comp. 30).

Workup

  1. stirringthe whole was stirred for 1 hour
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 99:1)
  7. customThe eluent of the desired fraction was evaporated
  8. customthe residue was triturated in methanol
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-4e07a72d9f9c490a8b780298df67225a
Source dataset
uspto-grants-1997_07
Patent number
US05650411

Reaction notes

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