Dimethylformamide → 4-Iodo-1-tritylimidazole

HRID 499020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 499020
[I:1]C1NC=CN=1.[C:7]1([C:13](Cl)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([N:29]([CH2:32]C)CC)C.C[N:35]([CH:37]=O)[CH3:36]>>[C:7]1([C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:29]2[CH:32]=[C:36]([I:1])[N:35]=[CH:37]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 27734682-iodo-1H-imidazole

Produkt 1

HCID 6182524-Iodo-1-tritylimidazole

Versuchsvorschrift

DMF, 100 mL, was stirred, and 13.2 grams (0.068 mole) of 5-iodoimidazole (vi) was added, followed by 18.9 grams (0.068 mole) of triphenylmethyl chloride, and 3.3 grams (0.033 mole) of triethylamine. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 18 hours. After this time, the reaction mixture was poured into crushed ice where it stirred until the ice melted. The resultant solid was then collected by filtration and triturated with diethyl ether. A solid was collected by filtration and washed with diethyl ether, yielding the subject compound. The diethyl ether filtrate was concentrated under reduced pressure to a residue, and re-triturated with diethyl ether, yielding additional subject compound. The total yield of subject compound was about 5.0 grams. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. additionUpon completion of addition
  2. additionAfter this time, the reaction mixture was poured
  3. custominto crushed ice where it
  4. filtrationThe resultant solid was then collected by filtration
  5. customtriturated with diethyl ether
  6. filtrationA solid was collected by filtration
  7. washwashed with diethyl ether
  8. customyielding the subject compound
  9. concentrationThe diethyl ether filtrate was concentrated under reduced pressure to a residue
  10. customre-triturated with diethyl ether
  11. customyielding additional subject compound

Quellen und Nachweise

ORD-Eintrag
ord-ca032cb3969648b6a1092708d389c2e9
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07767667B2

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