N-bromobutanimide → 908141-98-0

HRID 1784392Notes

Reaction equation

HRID 1784392 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[N:3]=1.[Br:14]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[Br:14][C:11]1[O:10][C:9]([C:4]2[CH:5]=[C:6]([Cl:8])[N:7]=[C:2]([Cl:1])[N:3]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 57592532HCID 57592532, compound

Product 1

HCID 57592517908141-98-0Yield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2,4-Dichloro-6-furan-2-yl-pyrimidine (1.44 g, 6.71 mmol) in DMF (20 ml) was added N-bromosuccinimide (1.31 g, 7.38 mmol) in a portionwise fashion. The resultant mixture was stirred at room temperature for a 2.5 hours before being diluted in EtOAc (50 ml) and washed with water (2×50 ml). The organic extract was dried (MgSO4), filtered and concentrated in vacuo to give an orange, semi-crystalline slurry. The crude residue was washed with ether and filtered to leave the desired product (1.29 g, 99%) as a whited crystalline solid in suitably clean form to be used without any further purification. m/z (LC-MSW, ESP):294 [M+H]+, R/T=5.09 mins.

Workup

  1. washwashed with water (2×50 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give an orange, semi-crystalline slurry
  7. washThe crude residue was washed with ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-aad6a35505cf413f8f81442d8ac5ff79
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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