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1,2-Dichloroethane → HCID 10109962, Verbindung

HRID 1182473
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1182473
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)=[O:12].[CH:22]1[CH:23]=[CH:24][C:25]2[N:30](O)N=[N:28][C:26]=2[CH:27]=1.C(Cl)CCl.C1(N)C=CC=CC=1N>CN(C=O)C>[NH2:28][C:26]1[CH:27]=[CH:22][CH:23]=[CH:24][C:25]=1[NH:30][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 7243O-PhenylenediamineHCID 757711-HydroxybenzotriazoleHCID 109459918-(2-NAPHTHYL)-8-OXOOCTANOIC ACID

Produkt 1

HCID 10109962HCID 10109962, VerbindungAusbeute 42,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

To a solution of 7-(2-naphthoyl)heptanoic acid 50 g (1.00 g, 3.52 mmol) in DMF (15 mL) were added HOBT (950 mg, 7.04 mmol) and EDC (1.00 g, 5.28 mmol). The mixture was stirred at room temperature for 1 hour, after which 1,2-phenylenediamine (760 mg, 7.04 mmol) was added and the solution was stirred at room temperature for 16 hours. The DMF was evaporated under high vacuum, deionized water was added, and the mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated sodium bicarbonate (20 mL), washed with brine (20 mL), and dried (MgSO4). The solvents were removed in vacuo and the title compound 63 (558 mg, 42%) was isolated by recrystallization from acetone and dichloromethane. 1H NMR (300 MHz, 20% CD3OD in CDCl3): δ 8.47 (s, 1H), 8.10-7.85 (m, 4H), 7.63-7.50 (m, 2H), 7.14-6.70 (m, 4H), 3.11 (t, J=7.2 Hz, 2H), 2.39 (t, J=7.5 Hz, 2H), 1.77 (m, 4H), 1.46 (m, 4H). 13C NMR (75 MHz, 20% CD3OD in CDCl3): δ 23.99, 25.40, 28.66, 28.74, 36.08, 38.23, 117.69, 119.09, 123.45, 124.01, 125.34, 126.53 126.86, 127.45, 128.19, 128.23, 129.28, 129.56, 132.23, 133.85, 135.32, 140.58, 172.81, 201.11.

Aufarbeitung

  1. stirringthe solution was stirred at room temperature for 16 hours
  2. customThe DMF was evaporated under high vacuum
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  5. washThe combined organic layers were washed with saturated sodium bicarbonate (20 mL)
  6. washwashed with brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. customThe solvents were removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2fa65f7cbfe84386a3a862d490b47865
Quelldatensatz
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07288567B2

Notizen zur Reaktion

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