Iodoethane → HCID 12813183, compound

HRID 1154983Notes

Reaction equation

HRID 1154983 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]2[C:13](=[O:14])[C:12]([C:15]3[CH:16]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:19][CH:20]=3)=[CH:11][NH:10]2)[CH:4]=1.[CH2:27](I)[CH3:28].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[F:26][C:2]([F:1])([F:25])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N:9]2[C:13](=[O:14])[C:12]([C:15]3[CH:16]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:19][CH:20]=3)=[CH:11][N:10]2[CH2:27][CH3:28])[CH:4]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 12813180HCID 12813180, compound

Product 1

HCID 12813183HCID 12813183, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 4 gram portion of 1,4-bis-(α,α,α-trifluoro-3-tolyl)-3-pyrazolin-5-one (from Example 4) was heated with 20 ml. ethyl iodide, 3 grams potassium carbonate, and 40 ml. ethanol at reflux temperature for about 4 hours. The reaction product mixture was concentrated in vacuo and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the drying agent filtered off and the filtrate concentrated in vacuo. On standing overnight the residue solidified and was recrystallized from a mixture of hexane and benzene. The solid was chromatographed on a silica gel column using a mixture of ethyl acetate and hexane in the ratio of 1:2. The product from the column was then recrystallized from a mixture of hexane and benzene to yield the desired product, m.p. 110°-111° C.

Workup

  1. concentrationThe reaction product mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationthe drying agent filtered off
  5. concentrationthe filtrate concentrated in vacuo
  6. customthe residue solidified and was recrystallized from a mixture of hexane and benzene
  7. customThe solid was chromatographed on a silica gel column
  8. additiona mixture of ethyl acetate and hexane in the ratio of 1:2
  9. customThe product from the column was then recrystallized from a mixture of hexane and benzene

Sources & evidence

ORD record
ord-889d6887f20e400288a44421f9d116f9
Source dataset
uspto-grants-1981_11
Patent number
US04299614

Reaction notes

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