Methyl iodide → HCID 73847915, compound

HRID 977623Notes

Reaction equation

HRID 977623 reaction equation
[F:1][C:2]([F:27])([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH2:18][F:19])([CH2:16][F:17])[CH:13]=[C:12]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=S)[C:11]=2[CH:26]=1)[C:3]([F:6])([F:5])[F:4].IC.[N+:30]([CH3:33])([O-:32])=[O:31].[H-].[Na+]>O1CCCC1>[F:1][C:2]([F:27])([C:7]1[CH:8]=[CH:9][C:10]2[O:15][C:14]([CH2:18][F:19])([CH2:16][F:17])[CH:13]=[C:12]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[CH:33][N+:30]([O-:32])=[O:31])[C:11]=2[CH:26]=1)[C:3]([F:6])([F:5])[F:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6375NitromethaneHCID 24758Sodium hydrideHCID 21831297HCID 21831297, compound

Product 1

HCID 73847915HCID 73847915, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.16 g of 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-thioxo-1-pyrrolidinyl)-2H-1-benzopyran, 0.78 g of iodomethane, 0.41 g of nitromethane and 6 ml of tetrahydrofuran was added 0.10 g of sodium hydride (60%) at room temperature with stirring. The mixture was refluxed with heating for 2 hours. After addition of ice water, the mixture was extracted with methylene chloride. The organic layer was washed with water and dried. The solvent was distilled off and the resultant residue was purified using silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 0.02 g of 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-nitromethylene-1-pyrrolidinyl)-2H-1-benzopyran represented by the following formula having a melting point of 195°-197° C.

Workup

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 2 hours
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe organic layer was washed with water
  5. customdried
  6. distillationThe solvent was distilled off
  7. customthe resultant residue was purified

Sources & evidence

ORD record
ord-4c4ec58fd6064d8aa270e42c77107f25
Source dataset
uspto-grants-1997_03
Patent number
US05614633

Reaction notes

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