N-bromobutanimide → HCID 86690308, compound

HRID 1428689Notes

Reaction equation

HRID 1428689 reaction equation
[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[CH:9][C:10]([NH2:20])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:3][CH:2]=1.[Br:22]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>CS(C)=O.O>[Br:22][C:9]1[C:10]([NH2:20])=[N:11][C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:21])=[CH:2][CH:3]=2)[N:8]=1

Participants

6

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 86690309HCID 86690309, compound

Product 1

HCID 86690308HCID 86690308, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 5,6-di-p-tolylpyrazin-2-amine (step 2) (4.94 g, 17.94 mmol) in DMSO (40 ml), was treated with N-bromosuccinimide (3.19 g, 17.94 mmol). The reaction mixture was stirred at room temperature for 2 hours to give a beige coloured suspension. The suspension was diluted with water (700 ml) and the pH was adjusted to pH 8-9 using a sat. NaHCO3 solution. The suspension was filtered, washed with water (×3) and dried under vacuum to afford the titled compound as a beige coloured solid;

Workup

  1. customto give a beige coloured suspension
  2. filtrationThe suspension was filtered
  3. washwashed with water (×3)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b9c888ca8ba440f28900275e31f329f5
Source dataset
uspto-grants-2015_01
Patent number
US08937069B2

Reaction notes

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