Methyl iodide → HCID 21831307, compound

HRID 1601406Notes

Reaction equation

HRID 1601406 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]#[C:31][NH2:32].[H-].[Na+]>O1CCCC1>[C:31]([N:32]=[C:21]1[CH2:22][CH2:23][CH2:24][N:20]1[C:12]1[C:11]2[CH:26]=[C:7]([C:2]([F:27])([F:1])[C:3]([F:6])([F:5])[F:4])[CH:8]=[CH:9][C:10]=2[O:15][C:14]([CH2:18][F:19])([CH2:16][F:17])[CH:13]=1)#[N:30]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 9864CyanamideHCID 24758Sodium hydrideHCID 21831297HCID 21831297, compound

Product 1

HCID 21831307HCID 21831307, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 0.05 g of 6-pentafluoroethyl-2,2-bisfluoromethyl-4-(2-thioxo-1-pyrrolidinyl)-2H-1-benzopyran, 0.20 g of iodomethane, 0.05 g of cyanamide and 3 ml of tetrahydrofuran was added 0.06 g of sodium hydride (60%) under ice-cooling with stirring. The mixture was stirred under ice-cooling for 30 minutes and then stirred at room temperature for 17 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 49 mg of 4-(2-cyanoimino-1-pyrrolidinyl)-6-pentafluoroethyl-2,2-bisfluoromethyl-2H-1-benzopyran represented by the following formula having a melting point of 207-210°C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred under ice-
  3. temperaturecooling for 30 minutes
  4. stirringstirred at room temperature for 17 hours
  5. extractionthe mixture was extracted with methylene chloride
  6. washThe organic layer was washed with water
  7. customdried
  8. distillationThe solvent was distilled off
  9. customthe resultant residue was purified

Sources & evidence

ORD record
ord-91e542d18a40479aacd38ba1ffacb150
Source dataset
uspto-grants-1999_11
Patent number
US05977167

Reaction notes

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