Water → Methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate

HRID 2411134Notes

Reaction equation

HRID 2411134 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Br:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.Cl[CH2:21][CH2:22][CH2:23][S:24](Cl)(=[O:26])=[O:25].O>C(Cl)Cl>[Br:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([N:1]2[CH2:21][CH2:22][CH2:23][S:24]2(=[O:26])=[O:25])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 17871390Methyl 2-Amino-4-bromobenzoate

Product 1

HCID 58484624Methyl 4-bromo-2-(1,1-dioxoisothiazolidin-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-amino-4-bromobenzoate (5 g) and triethylamine (5.73 mL) were dissolved in methylene chloride (39 mL), 3-chloropropane-1-sulfonyl chloride (3.44 mL) was added under ice-cooling, and the mixture was stirred at room temperature. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with dilute hydrochloric acid and saturated brine, and the solvent was evaporated. To the obtained residue were added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)(3.9 mL) and N,N-dimethylformamide (29 mL), and the mixture was stirred at room temperature. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and saturated brine, and the solvent was evaporated. To the obtained residue was added diisopropyl ether, and the precipitate was collected by filtration to give the title compound (5.05 g).

Workup

  1. temperaturecooling
  2. additionwas added to the reaction mixture
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with dilute hydrochloric acid and saturated brine
  5. customthe solvent was evaporated
  6. additionTo the obtained residue were added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)(3.9 mL) and N,N-dimethylformamide (29 mL)
  7. stirringthe mixture was stirred at room temperature
  8. customAfter completion of the reaction, water
  9. additionwas added to the reaction mixture
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe organic layer was washed with dilute hydrochloric acid and saturated brine
  12. customthe solvent was evaporated
  13. additionTo the obtained residue was added diisopropyl ether
  14. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4c6b463126d94799b9350cac284e9bda
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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