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Triethylamine → 3-(4-Ethylthio-5-(4-methyl-1,2-dioxocyclobut-3-en-3-yl)amino-3-indolyl)1-propanol

HRID 441101
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 441101
[NH2:1][C:2]1[C:3]([S:15][CH2:16][CH3:17])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][OH:14].Cl[C:19]1[C:20](=[O:25])[C:21](=[O:24])[C:22]=1[CH3:23].CCN(CC)CC.[K+].[Br-]>CN(C=O)C.O>[CH2:16]([S:15][C:3]1[C:2]([NH:1][C:19]2[C:20](=[O:25])[C:21](=[O:24])[C:22]=2[CH3:23])=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH2:11][CH2:12][CH2:13][OH:14])=[CH:6][NH:7]2)[CH3:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 253877Potassium BromideHCID 126143603-Chloro-4-methylcyclobut-3-ene-1,2-dioneHCID 224056733-(5-Amino-4-ethylthio-3-indolyl)-1-propanol

Produkt 1

HCID 224057163-(4-Ethylthio-5-(4-methyl-1,2-dioxocyclobut-3-en-3-yl)amino-3-indolyl)1-propanol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

A mixture of 3-(5-amino-4-ethylthio-3-indolyl)-1-propanol (0.93 g, 3.7 mmol), 3-chloro-4-methyl-1,2-dioxocyclobut-3-ene (0.58 g, 4.4 mmol) and Et3N (0.62 ml, 4.4 mmol) in DMF (50 ml) was stirred at 23° C. for 50 h before adding water (200 ml). The aqueous solution was extracted with EtOAc (3×75 ml). The organic extracts were washed with water (50 ml), dried (MgSO4) and concentrated in vacuo. The crude material was purified on silica gel dry column using first a mixture of CH2Cl2 :EtOAc (1:4) and then EtOAc:Et3N (49:1). Appropriate fractions were concentrated in vacuo leaving yellow crystals, 0.815 g, m.p. 119° C., 64%. 1H NMR (DMSO-d6) δ (ppm): 11.17, 11.11, 10.80 and 10.51 (4 br s, 2H indolic NH, and 5-NH), 7.4 (br s, 1H), 7.26 (s, 1H), 7.07 (d, J=8.2 Hz, 1H), 4.40 (t, J=5.2 Hz, 1H, OH), 3.46 (t, J=3.5 Hz, 2H after D2O exchange), 2.95-3.10 (m, 2H, CH2CH2CH2O), 2.66 (br s, 2H, CH3CH 2 S), 2.26 (br s, 1H, CH3 on dioxocyclobutene), 1.7-1.9 (m, 2H, CH2CH2CH2O), 1.59 (br s, 2H, CH3 on dioxocyclobutene), 0.9-1.1 (m, 3H, CH3CH2S). IR (KBr) n:3420, 3300-3000, 1775, 1728, 1620, 1580 and 1400 cm-1. Anal. calcd. for: C18H20N2O3S: C 62.77; H 5.85; N 8.13; S 9.31. Found: C 62.75; H 5.85; N 8.20; S 9.25.

Aufarbeitung

  1. extractionThe aqueous solution was extracted with EtOAc (3×75 ml)
  2. washThe organic extracts were washed with water (50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified on silica gel
  6. customdry column
  7. additiona mixture of CH2Cl2 :EtOAc (1:4)
  8. concentrationAppropriate fractions were concentrated in vacuo
  9. customleaving yellow crystals, 0.815 g, m.p. 119° C., 64%

Quellen und Nachweise

ORD-Eintrag
ord-a0ab3789bf444a6594190f96e100947e
Quelldatensatz
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05521188

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