Hydrochloric Acid → Ethyl 3-methylsulphanyl-2-oxo-2,3-dihydro-1H-indole-5-carboxylate

HRID 1093986

반응식

HRID 1093986 반응식
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][S:14][CH2:15][C:16](OCC)=[O:17].C(OCl)(C)(C)C.Cl>C(Cl)Cl.CCOCC.C(N(CC)CC)C>[CH3:13][S:14][CH:15]1[C:3]2[C:2](=[CH:12][CH:11]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=2)[NH:1][C:16]1=[O:17]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochlorite

생성물 1

HCID 12351489Ethyl 3-methylsulphanyl-2-oxo-2,3-dihydro-1H-indole-5-carboxylate

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

반응 조건

온도
-50 °C

실험 절차

To a solution of ethyl 4-amino-benzoate (40.0 g) in DCM (900 ml) at −60° C. there is added, dropwise, ethyl (methylsulphanyl)acetate (34.5 ml) under a nitrogen atmosphere. 29.0 g of tBuOCl are then added, dropwise, to the reaction mixture over 25 minutes, maintaining the temperature between −60° C. and −55° C. After stirring for one hour at −50° C., triethylamine (15.4 ml) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (485 ml) is added dropwise. After stirring for 12 hours at ambient temperature, the phases are separated and the organic phase is washed successively with aq. 2M HCl solution, water and then sat. aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The residue obtained is taken up in ether. The crystals obtained are filtered off, washed with ether and dried in vacuo to yield the title product, which is used directly in the next Step.

후처리

  1. temperaturemaintaining the temperature between −60° C. and −55° C
  2. customis brought to 0° C.
  3. stirringAfter stirring for 12 hours at ambient temperature
  4. customthe phases are separated
  5. washthe organic phase is washed successively with aq. 2M HCl solution, water
  6. dry with materialThe organic phase is dried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe residue obtained
  10. customThe crystals obtained
  11. filtrationare filtered off
  12. washwashed with ether
  13. customdried in vacuo

출처 및 근거

ORD 기록
ord-6a870c69599a4d95933929a320c9406f
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133889B2

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