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

HRID 1804063노트

반응식

HRID 1804063 반응식
[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

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 17871390Methyl 2-Amino-4-bromobenzoate

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d9f004fcb7054bffbb543cbfdd147709
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354401B2

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