N-bromobutanimide → HCID 22721993, compound

HRID 1581508Notes

Reaction equation

HRID 1581508 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[NH:4][N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=1.[Br:15]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:3](=[O:14])[NH:4][N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:7]=1[Br:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 105594874-amino-6-phenyl-2H-pyridazin-3-one

Product 1

HCID 22721993HCID 22721993, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Amino-6-phenyl-3(2H)-pyridazinone (prepared by the method of Example 1a), or according to McKillop et al., Heterocycles, 1989, 29(6), 1077) (4.69 g, 25 mmol) and N-bromosuccinimide (4.50 g, 25.3 mmol), suspended in dry acetonitrile (135 ml), was heated at reflux under a nitrogen atmosphere for 6 hours, then allowed to stand at room temperature for 18 hours. The solid was collected by filtration, washed with ethyl acetate (40 ml) and diethyl ether (40 ml), and dried in vacuo at 60° C., to afford the title compound, 6.25 g (94%), as a colourless solid. 1H NMR (400 MHz, DMSO-d6) δ12.93 (1H, s), 7.43 (5H, m), 6.69 (2H, br s); m/e (ES+) 266/268 [MH]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under a nitrogen atmosphere for 6 hours
  3. filtrationThe solid was collected by filtration
  4. washwashed with ethyl acetate (40 ml) and diethyl ether (40 ml)
  5. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-7df452dce7f44f9b902746957c0bb902
Source dataset
uspto-grants-2004_05
Patent number
US06730676B2

Reaction notes

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