Bromine → HCID 67455457, compound

HRID 639687Notes

Reaction equation

HRID 639687 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([N:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]=2[NH:10][C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:38]Br>C(O)(=O)C.O>[CH2:1]([N:8]1[C:16]2[C:15]([Br:38])=[CH:14][N:13]=[C:12]([N:17]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:11]=2[NH:10][C:9]1=[O:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 67455786HCID 67455786, compound

Product 1

HCID 67455457HCID 67455457, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1-benzyl-4-dibenzylamino-1,3-dihydro-imidazo[4,5,c]pyridine-2-one (1 g, 2.4 mmol) was suspended in 20 mL of acetic acid then sodium acetate (195 mg, 2.4 mmol) was added followed by bromine (456 mg, 2.85 mmol) dropwise. The mixture was stirred at room temperature for 15 minutes. A heavy precipitate was formed. The mixture was diluted in water (50 mL) and the solid was filtered and washed with water. It was then diluted in ethyl acetate (20 mL), dried over magnesium sulfate and the solvent was removed in vacuo to give 1.29 g of the title compound as a light orange solid.

Workup

  1. customA heavy precipitate was formed
  2. filtrationthe solid was filtered
  3. washwashed with water
  4. additionIt was then diluted in ethyl acetate (20 mL)
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a8f21b95dd714688ab5d5c63bef895d5
Source dataset
uspto-grants-2010_04
Patent number
US07691877B2

Reaction notes

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