Methyl iodide → HCID 21831307, compound

HRID 363466Notes

Reaction equation

HRID 363466 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-tooling 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-tooling for 30 minutes
  3. stirringstirred at room temperature for 17 hours
  4. extractionthe mixture was extracted with methylene chloride
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationThe solvent was distilled off
  8. customthe resultant residue was purified

Sources & evidence

ORD record
ord-39d11f488a0844c68a9ab4bfc37e3421
Source dataset
uspto-grants-1999_02
Patent number
US05874446

Reaction notes

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