Water → HCID 136403394, compound

HRID 359708Notes

Reaction equation

HRID 359708 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]3[CH2:22][CH2:21][CH2:20][N:12]3[C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.B(Br)(Br)[Br:24].O>C(Cl)Cl>[BrH:24].[BrH:24].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]3[CH2:22][CH2:21][CH2:20][N:12]3[C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 4690382-(4-Methoxyphenyl)-3-(4-pyridyl)-6,7-dihydro-(5H)-pyrrolo(1,2-a)imidazole

Product 1

HCID 136403394HCID 136403394, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 3g (10.3 mmoles) of 2-(4-methoxyphenyl)-3-(4-pyridyl)-6,7-dihydro [5H]pyrrolo [1,2-a]imidazole of Part c) above in 150 ml of dry methylene chloride was treated dropwise at -80° C. with a solution of 17.7 g (30.9 mmoles) of boron tribromide in methylene chloride and allowed to warm to room temperature overnight. The reaction mixture was chilled in an ice bath, 5 to 10 ml of water added, and the solvent removed in vacuo. The residue was recrystallized from hot water containing 0.5 ml. of 48% hydrobromic acid and dried in vacuo to afford the titled compound as bright yellow crystals, mp 257-258° C. Anal. Calcd. for C1H15N3O2HBr.1/3H20: C, 45.87; H, 4.00; N, 9.44. Found: C,45.66; H, 3.69; N,9.67.

Workup

  1. temperatureThe reaction mixture was chilled in an ice bath
  2. customthe solvent removed in vacuo
  3. customThe residue was recrystallized from hot water containing 0.5 ml
  4. dry with materialof 48% hydrobromic acid and dried in vacuo

Sources & evidence

ORD record
ord-1eeb06a6997040e1a84108a469ec4837
Source dataset
uspto-grants-1991_03
Patent number
US05002941

Reaction notes

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