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

HRID 44266

Reaktionsgleichung

Reaktionsgleichung von HRID 44266
[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.C([O:15][C:16](=O)[CH2:17][S:18][CH3:19])C.C(OCl)(C)(C)C.Cl>C(Cl)Cl.CCOCC.C(N(CC)CC)C>[CH3:19][S:18][CH:17]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:15]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
-50 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-506deeb5f54946d7a3c2fa62f0204408
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541412B2

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