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Toluene → HCID 178509087, Verbindung

HRID 57761
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 57761
C1(C)C=CC=CC=1.[F:8][C:9]([F:14])([F:13])[C:10]([OH:12])=[O:11].O=[C:16]([CH2:36][CH2:37][CH2:38][CH2:39][C:40](=O)[CH2:41][NH:42]/[C:43](/[NH:52]C(OC(C)(C)C)=O)=[N:44]\C(OC(C)(C)C)=O)[CH2:17][NH:18]/[C:19](/[NH:28]C(OC(C)(C)C)=O)=[N:20]\C(OC(C)(C)C)=O>O>[F:8][C:9]([F:14])([F:13])[C:10]([O-:12])=[O:11].[CH2:39]([C:40]1[NH+:44]=[C:43]([NH2:52])[NH:42][CH:41]=1)[CH2:38][CH2:37][CH2:36][C:16]1[NH+:20]=[C:19]([NH2:28])[NH:18][CH:17]=1.[F:8][C:9]([F:14])([F:13])[C:10]([O-:12])=[O:11]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 6422Trifluoroacetic acid2×HCID 178454273(E,E)-1,1'-(2,7-Dioxooctane-1,8-diyl)bis(2',3-dibocguanidine)

Produkt 1

HCID 178509087HCID 178509087, VerbindungAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Toluene (40 mL) and trifluoroacetic acid (650 μL, 8.36 mmol, 10.0 equiv) were added via syringe to a flask charged with ketoguanidine 75 (549 mg, 0.836 mmol, 1 equiv) and the resulting mixture was heated to 75° C. After 16 h, the reaction mixture was allowed to cool to 23° C. and was concentrated under reduced pressure. Water (20 mL) and trifluoroacetic acid (650 μL, 8.36 mmol, 10.0 equiv) were added via syringe to the residue and the resulting mixture was heated to 100° C. After 45 h, the reaction mixture was allowed to cool to 23° C. and was concentrated under reduced pressure to give 2-aminoimidazole 76 (375 mg, 100%) as a brown solid. 1H NMR (500 MHz, CD3OD, 21° C.): δ 6.49 (s, 2H), 2.53 (app-t, J=6.5 Hz, 4H), 1.65 (app-t, J=7.1 Hz, 4H). 13C NMR (125.8 MHz, CD3OD, 21° C.): δ 162.6, 148.8, 128.8, 109.8, 101.4, 28.7, 25.2. FTIR (neat) cm−1: 3179 (br-s), 2361 (w), 1702 (s), 1442 (m), 1205 (s), 1134 (s), 845 (m), 723 (m). HRMS (ESI) (m/z): calc'd for C10H17N6, [M+H]+: 221.1509, found: 221.1512.

Aufarbeitung

  1. temperatureto cool to 23° C.
  2. concentrationwas concentrated under reduced pressure
  3. temperaturethe resulting mixture was heated to 100° C
  4. waitAfter 45 h
  5. temperatureto cool to 23° C.
  6. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2c0f602285974419b8294d5dc12bc57d
Quelldatensatz
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09434736B2

Notizen zur Reaktion

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