Dimethylformamide → 4-Iodo-1-tritylimidazole

HRID 2220177Notes

Reaction equation

HRID 2220177 reaction equation
[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

Participants

5

Reactant 4

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

Product 1

HCID 6182524-Iodo-1-tritylimidazole

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6890e701de3048d6b53ff75e56a0df8d
Source dataset
uspto-grants-2008_08
Patent number
US07417057B2

Reaction notes

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