2-Aminobenzenesulfonamide → 2-(5-Bromo-2-chloropyrimidin-4-ylamino)benzenesulfonamide

HRID 2424372Notes

Reaction equation

HRID 2424372 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([NH2:20])(=[O:19])=[O:18].C(=O)([O-])O.[Na+]>CC(O)C.Cl>[Br:1][C:2]1[C:3]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[S:17]([NH2:20])(=[O:18])=[O:19])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 728942-AminobenzenesulfonamideHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 516892Sodium Bicarbonate

Product 1

HCID 859979922-(5-Bromo-2-chloropyrimidin-4-ylamino)benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-bromo-2,4-dichloropyrimidine (300 mg, 1.32 mmol) and 2-amino-benzenesulfonamide (340 mg, 1.97 mmol) in 2-propanol (3 mL), concentrated hydrochloric acid (0.06 mL) is added and the mixture is stirred at 90° C. for 4.5 hours. The mixture is poured into aqueous sodium hydrogen carbonate and extracted with ethyl acetate three times. The organic layer is washed with water, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by column chromatography (hexane:ethyl acetate=2:1) to afford the title compound.

Workup

  1. extractionextracted with ethyl acetate three times
  2. washThe organic layer is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue is purified by column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-9ba9abeff4444547803d41d037ddf6a7
Source dataset
uspto-grants-2011_06
Patent number
US07964592B2

Reaction notes

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