Triethylamine → Dibenzothiazepinone

HRID 625175

Reaktionsgleichung

Reaktionsgleichung von HRID 625175
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11](O)=[O:12].CCN=C=NCCCN(C)C.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1>ClCCl>[CH:14]1[C:10]2[C:11](=[O:12])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8][C:9]=2[CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 109558282-((2-Aminophenyl)thio)benzoic acid

Produkt 1

HCID 374829Dibenzothiazepinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-((2-aminophenyl)thio)benzoic acid, prepared as described in the previous step, (30 g, 0.122 mol) in dichloromethane (300 mL) was added EDCI (35.2 g, 0.183 mol), triethylamine (51 mL, 0.366 mol) and HOBT (24.7 g, 0.183 mol). The reaction mixture was stirred at room temperature for 12 hours, washed with 1M aq.HCl, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, and dried over MgSO4. The solution was filtered, concentrated, and purified by column chromatography to provide the title compound. ESI-MS (M+1): 228 calc. for C13H9NOS 227. 1H NMR: (CDCl3, 400 MHz): δ (ppm) 7.70-7.67 (m, 1H), 7.58-7.52 (m, 2H), 7.50-7.42 (m, 2H), 7.39-7.35 (m, 1H), 7.24-7.22 (m, 1H), 7.17-7.13 (m, 1H).

Aufarbeitung

  1. washwashed with 1M aq
  2. dry with materialHCl, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, and dried over MgSO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c8b477fb6385461789e5e7bab31d73ee
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09304126B2

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