Water → HCID 15035600, compound

HRID 1461409Notes

Reaction equation

HRID 1461409 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH:29]=[CH:28][N:27]([CH3:30])[C:26]4=[O:31])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[CH:9][CH:8]=1.O.[OH-].[NH4+]>ClCCl.CO>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[CH:20]=[CH:21][C:22]([N:25]4[CH:29]=[CH:28][N:27]([CH3:30])[C:26]4=[O:31])=[CH:23][CH:24]=3)[CH2:17][CH2:18]2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 19980374HCID 19980374, compound

Product 1

HCID 15035600HCID 15035600, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and cooled (ice-bath) amount of 200 ml of a boron tribromide solution in dichloromethane 1M was added dropwise a solution of 14.6 parts of 1,3-dihydro-1-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-3-methyl-2H-imidazol-2-one in 665 parts of dichloromethane. Stirring was continued for 5 days at room temperature and then the reaction mixture was poured into a mixture of 200 parts of water, 158 parts of methanol and 180 parts of ammonium hydroxide. After stirring for 1 hour, the precipitate was filtered off, washed with dichloromethane and water and dried (=first fraction of product). The organic layer of the filtrate was separated and evaporated. The residue was triturated in dichloromethane. The solid was filtered off and dried (=second fraction). The two fractions were combined and crystallized from N,N-dimethylformamide, yielding 9.6 parts (68.5%) of 1,3-dihydro-1-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3-methyl-2H-imidazol-2-one; mp. 283.1° C. (interm. 14).

Workup

  1. stirringStirring
  2. stirringAfter stirring for 1 hour
  3. filtrationthe precipitate was filtered off
  4. washwashed with dichloromethane and water
  5. customdried (=first fraction of product)
  6. customThe organic layer of the filtrate was separated
  7. customevaporated
  8. customThe residue was triturated in dichloromethane
  9. filtrationThe solid was filtered off
  10. customdried (=second fraction)
  11. customcrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-5a02ac6b99b84221a24f2059e0a888a2
Source dataset
uspto-grants-1991_12
Patent number
US05075309

Reaction notes

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