Iodoethane → HCID 12392672, compound

HRID 926900Notes

Reaction equation

HRID 926900 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)[CH3:2].[I:8][CH2:9][CH3:10]>C(OCC)(=O)C>[I-:8].[CH2:1]([N+:3]1[CH:7]=[CH:6][N:5]([CH2:9][CH3:10])[CH:4]=1)[CH3:2]

Participants

4

Procedure

1-ethylimidazole (4.81 g, 50 mmol, Sigma-Aldrich, 99%) in 50 mL ethyl acetate was cooled to 0° C. in an ice bath. Once cool, iodoethane (8.69 g, 55.7 mmol, Sigma-Aldrich, 99%) was added dropwise via an addition funnel. The solution was allowed to warm slowly to room temperature then stirred overnight. The precipitate was filtered off and washed with diethyl ether. The filtrate was collected and an additional 8.96 g (57.4 mmol) iodoethane was added and stirring continued at room temperature for 6 days. The solution was filtered again and the residue was washed with diethyl ether. The combined solids were dried overnight under high vacuum yielding 9.76 g white solids (38.7 mmol, 77% yield) that were used without further purification.

Workup

  1. temperatureOnce cool
  2. filtrationThe precipitate was filtered off
  3. washwashed with diethyl ether
  4. customThe filtrate was collected
  5. stirringstirring
  6. waitcontinued at room temperature for 6 days
  7. filtrationThe solution was filtered again
  8. washthe residue was washed with diethyl ether
  9. customThe combined solids were dried overnight under high vacuum

Sources & evidence

ORD record
ord-c25113cd3dec40e0b5f318195503c45d
Source dataset
uspto-grants-2016_03
Patent number
US09289757B2

Reaction notes

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