Ammonia → HCID 178474184, Verbindung

HRID 559565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 559565
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=S)=[CH:4][CH:3]=1.CI.N.CO.[CH2:20]([N:22](CC)CC)[CH3:21].C(Cl)(=[O:29])C>CC#N.CN(C=O)C.N1C=CC=CC=1.C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10]/[C:9]/2=[N:22]\[C:20](=[O:29])[CH3:21])=[CH:4][CH:3]=1

Komponenten

11

Edukt 6

HCID 222AmmoniaHCID 887MethanolHCID 6328Methyl iodideHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86616333HCID 86616333, Verbindung

Produkt 1

HCID 178474184HCID 178474184, VerbindungAusbeute 28,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-(4-iodophenyl)pyridine-2(1H)-thione (384 mg, 1.23 mmol) in CH3CN (10 mL), CH3I (0.80 mL, 12.8 mmol) was added. After being stirred at room temperature overnight, the mixture was concentrated in vacuo to give a solid. The solid was dissolved in DMF (6 mL). To the solution, NH3 in MeOH (7N, 3.0 mL, 21.0 mmol) and triethylamine (1.5 mL, 10.8 mmol) were added. After being stirred at room temperature overnight, the mixture was purified by HPLC to give a solid. The solid was dissolved in pyridine (3 mL) and CH2Cl2 (3 mL). To the solution, acetyl chloride (0.200 mL, 2.8 mmol) was added. After being stirred at room temperature overnight, the mixture was purified by HPLC to give (E)-N-(1-(4-iodophenyl)pyridin-2(1H)-ylidene)acetamide (120 mg).

Aufarbeitung

  1. concentrationthe mixture was concentrated in vacuo
  2. customto give a solid
  3. stirringAfter being stirred at room temperature overnight
  4. customthe mixture was purified by HPLC
  5. customto give a solid
  6. stirringAfter being stirred at room temperature overnight
  7. customthe mixture was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9b43f3ab1b4844c1a0b6cab4b79004bf
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063077B2

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