Trifluoroiodomethane → HCID 13340634, compound

HRID 1632731Notes

Reaction equation

HRID 1632731 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:22])[CH:11]=[CH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[F:32][C:33](I)([F:35])[F:34]>>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[CH:12]=[C:11]([C:33]([F:35])([F:34])[F:32])[N:10]([CH3:22])[C:9]=2[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 3

HCID 16843TrifluoroiodomethaneHCID 81531DiisopropylethylamineHCID 133406332,3-Bis(4-methoxyphenyl)-1-methyl-1H-pyrrole

Product 1

HCID 13340634HCID 13340634, compound

Procedure

In a pressure reaction vessel was placed 2.9 g (0.01 mole) of 2,3-bis(4-methoxyphenyl)-1-methyl-1H-pyrrole and 1.3 g (0.01 mole) of ethyl diisopropylamine. The vessel was cooled and evacuated, and 2.0 g (0.01 mole) of trifluoromethyl iodide was added. The mixture was heated at 150° for approximately 18 hours. The vessel was cooled and vented, and the contents rinsed out with methylene chloride. The methylene chloride solution was washed with water three times then dried and concentrated to give the crude product. This was purified by chromatography on 400 g silica gel, eluting with toluene, to give after recrystallization from hexane, 1.0 g (28%) of product as a white solid, m.p. 125°-126°.

Workup

  1. customIn a pressure reaction vessel
  2. temperatureThe vessel was cooled
  3. customevacuated
  4. temperatureThe mixture was heated at 150° for approximately 18 hours
  5. temperatureThe vessel was cooled
  6. washthe contents rinsed out with methylene chloride
  7. washThe methylene chloride solution was washed with water three times
  8. customthen dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-acf88cb7b2f944d5bc6e0ed3b98e8204
Source dataset
uspto-grants-1984_10
Patent number
US04477463

Reaction notes

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