Triethylamine → Methyl 4-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)benzoate

HRID 2411139Notes

Reaction equation

HRID 2411139 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.C(N(CC)CC)C.Cl[CH2:22][CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[O:26]=[S:25]1(=[O:27])[CH2:24][CH2:23][CH2:22][N:2]1[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochloride

Product 1

HCID 43620001Methyl 4-(1,1-dioxo-1lambda6-isothiazolidin-2-ylmethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 4-aminomethylbenzoate hydrochloride (1.61 g) and triethylamine (2.45 mL) were dissolved in dichloromethane (40 mL), 3-chloropropane-1-sulfonyl chloride (1.17 mL) was added under ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, the solvent was evaporated, 1N hydrochloric acid was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was dissolved in N,N-dimethylformamide (8 mL), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1.46 mL) was added, and the mixture was stirred at room temperature overnight. To the reaction mixture was added 0.5N hydrochloric acid, and the mixture was extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:ethyl acetate) to give the title compound (1.95 g).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. addition1N hydrochloric acid was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. customthe solvent was evaporated
  8. dissolutionThe obtained residue was dissolved in N,N-dimethylformamide (8 mL)
  9. addition1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (1.46 mL) was added
  10. stirringthe mixture was stirred at room temperature overnight
  11. additionTo the reaction mixture was added 0.5N hydrochloric acid
  12. extractionthe mixture was extracted with ethyl acetate
  13. washthe organic layer was washed with water and saturated brine
  14. customthe solvent was evaporated
  15. customThe obtained residue was purified by column chromatography (chloroform:ethyl acetate)

Sources & evidence

ORD record
ord-8dffec6a754d4a0eb048bdab069a9d23
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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