N-Bromosuccinamide → HCID 24859292, compound

HRID 237414Notes

Reaction equation

HRID 237414 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[NH:7][C:8]([NH:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[CH:13][CH:12]=1)=[O:9].[Br:21]NC(=O)CCC(N)=O>C(#N)C>[Br:21][C:12]1[CH:13]=[N:14][C:15]2[C:20]([C:11]=1[NH:10][C:8]([NH:7][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][N:1]=1)=[O:9])=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

4

Reactant 2

HCID 9834204N-BromosuccinamideHCID 24772168HCID 24772168, compound

Product 1

HCID 24859292HCID 24859292, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(Pyrazin-2-yl)-3-(quinolin-4-yl)urea (220 mg, 0.754 mmol) was dissolved in acetonitrile (3 mL) and N-bromosuccinamide was added (201 mg, 1.13 mmol). The resulting solution was heated at 80 C under microwave irradiation for 35 mins. The cooled solution was then partitioned between NaHCO3 solution and dichloromethane. The organic layer was separated, dried (MgSO4), filtered and concentrated to give the product. Yellow solid. Amount 204 mg. Yield 79%.

Workup

  1. temperatureThe resulting solution was heated at 80 C under microwave irradiation for 35 mins
  2. customThe cooled solution was then partitioned between NaHCO3 solution and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the product

Sources & evidence

ORD record
ord-0fdde0bd715c4a05a7a9c7dfee8e8e4e
Source dataset
uspto-grants-2014_02
Patent number
US08642598B2

Reaction notes

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