4-Bromoaniline → HCID 18009142, compound

HRID 987555Notes

Reaction equation

HRID 987555 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[Br:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1>C1S(=O)(=O)CCC1>[Cl:8][C:6]1[CH:7]=[C:2]([NH:14][C:13]2[CH:15]=[CH:16][C:10]([Br:9])=[CH:11][CH:12]=2)[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 78074-BromoanilineHCID 709434,6-Dichloropyrimidine

Product 1

HCID 18009142HCID 18009142, compoundYield 11.1%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

4,6-Dichloropyrimidine (3.0 g, 20 mmol) was mixed with 4-bromoaniline (3.3 g, 19 mmol) and heated to 125° C. for two hours in tetramethylene sulphone. After cooling the reaction mixture was partitioned between saturated aqueous sodium bicarbonate solution and EtOAc. The organic portion was washed, dried over sodium sulphate, filtered and evaporated. The residue was purified by column chromatography (EtOAc (20%): isohexane) to yield a solid (0.6 g, 11%). M/z 284 (MH)+.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customwas partitioned between saturated aqueous sodium bicarbonate solution and EtOAc
  3. washThe organic portion was washed
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (EtOAc (20%): isohexane)

Sources & evidence

ORD record
ord-92cbfa703c2c403bb1ee0ef82665b41f
Source dataset
uspto-grants-2003_10
Patent number
US06632820B1

Reaction notes

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