Trifluoroacetic acid → N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]indoline-2-carboxamide

HRID 2082408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2082408
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[N:11]=[C:12]([NH:15][C:16]([CH:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]2C(OC(C)(C)C)=O)=[O:17])[S:13][CH:14]=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[N:11]=[C:12]([NH:15][C:16]([CH:18]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19]2)=[O:17])[S:13][CH:14]=1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 21249482N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]-1-tert-butoxycarbonyl-indoline-2-carboxamide

Produkt 1

HCID 21249485N-[4-(2,4,6-Trimethylphenyl)-2-thiazolyl]indoline-2-carboxamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

35 g of N-[4-(2,4,6-trimethylphenyl)-2-thiazolyl]-1-tert-butoxycarbonyl-indoline-2-carboxamide are dissolved in 200 ml of dry dichloromethane and 40 ml of trifluoroacetic acid are added dropwise. The reaction mixture is kept at ambient temperature for 2 hours and then evaporated to dryness. The residue obtained is taken up in 150 ml of ethyl acetate. The organic solution is washed with 1N aqueous sodium hydroxide solution and then with water saturated with NaCl and dried over anhydrous magnesium sulphate. After removal of the ethyl acetate, the final product is obtained, from which the salt is prepared by the action of gaseous HCl in isopropanol. The hydrochloride melts at 212° C. Yield 88%. Salt: 1H NMR: 80 MHz(DMSOd6) δ(ppm): 2.1(s,6H); 2.4(s,3H); 3.2-3.8(m,2H); 5.0(m,1H); 6.0(s,1H; 6.9-7.6(m,7H); 12.1(s,1H).

Aufarbeitung

  1. customevaporated to dryness
  2. customThe residue obtained
  3. washThe organic solution is washed with 1N aqueous sodium hydroxide solution
  4. dry with materialwith water saturated with NaCl and dried over anhydrous magnesium sulphate
  5. customAfter removal of the ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-56b28b0be4944494aee74a2b0ed9286d
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05189049

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