Hydrochloric Acid → HCID 59019548, Verbindung

HRID 970321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970321
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].I[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.CN1CCOCC1.Cl>CC(O)C(O)C.Cl[Cu]>[C:18]1([CH3:21])[CH:19]=[CH:20][C:15]([NH:1][C:2]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 122074-IodotolueneHCID 27248222-Aminoterephthalic acid

Produkt 1

HCID 59019548HCID 59019548, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 2622,3-ButanediolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a mixture of 2-amino-terephthalic acid (2.5 g, 23.8 mmol) and 1-iodo-4-methyl-benzene (7.78 g, 35.7 mmol) in butane-2,3-diol (38 mL) was added Cu (24 mg, 0.016 mmol), CuCl (950 mg, 9.6 mmol), and n-methyl morpholine (6.5 mL) under argon. The mixture was heated at 150° C. for 18 h. The reaction mixture was cooled to room temperature and HCl (0.1 N, 100 mL) was added. The resulting yellow precipitate was collected by filtration and triturated in a mixture of Et2O and EtOAc (1:1, 50 mL) for 1 h. The yellow solid was filtered, washed with ether (25 mL), and dried in vacuo to give 2.4 of 138A. HPLC retention time=3.046 min., condition A.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationThe resulting yellow precipitate was collected by filtration
  3. customtriturated in a mixture of Et2O and EtOAc (1:1, 50 mL) for 1 h
  4. filtrationThe yellow solid was filtered
  5. washwashed with ether (25 mL)
  6. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-47cc4bc63a3c4d10875cfc204faaee5e
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07312209B2

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