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

HRID 1804063Notes

Reaction equation

HRID 1804063 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.C(Cl)Cl.Cl[CH2:24][CH2:25][CH2:26][S:27](Cl)(=[O:29])=[O:28]>O>[Br:12][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([N:1]2[CH2:24][CH2:25][CH2:26][S:27]2(=[O:29])=[O:28])[CH:11]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 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 962WaterSolvent

Procedure

To a mixture of methyl 2-amino-4-bromobenzoate (5 g), triethylamine (5.73 mL), methylene chloride (39 mL) was added 3-chloropropanesulfonyl chloride (3.44 mL) under ice-cooling, and the mixture was stirred at room temperature. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with diluted hydrochloric acid and saturated brine, and the solvent was evaporated. To the residue were added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (3.9 mL) and DMF (29 mL), and the mixture was stirred at room temperature. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with diluted hydrochloric acid and saturated brine, and the solvent was evaporated. To the residue was added isopropyl ether, and the precipitated solid was collected by filtration to give the title compound (5.045 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with diluted hydrochloric acid and saturated brine
  4. customthe solvent was evaporated
  5. additionTo the residue were added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (3.9 mL) and DMF (29 mL)
  6. stirringthe mixture was stirred at room temperature
  7. additionWater was added to the reaction mixture
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with diluted hydrochloric acid and saturated brine
  10. customthe solvent was evaporated
  11. additionTo the residue was added isopropyl ether
  12. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-d9f004fcb7054bffbb543cbfdd147709
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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