Methyl iodide → HCID 21831299, compound

HRID 1601396Notes

Reaction equation

HRID 1601396 reaction equation
[F:1][CH2:2][C:3]1([CH2:23][F:24])[CH:8]=[C:7]([N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=S)[C:6]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:5]=2[O:4]1.CI.[N:27]#[C:28][NH2:29].[H-].[Na+]>C(Cl)Cl.O1CCCC1>[C:28]([N:29]=[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][N:9]1[C:7]1[C:6]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:5]=2[O:4][C:3]([CH2:23][F:24])([CH2:2][F:1])[CH:8]=1)#[N:27]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 9864CyanamideHCID 24758Sodium hydrideHCID 21831322HCID 21831322, compound

Product 1

HCID 21831299HCID 21831299, compoundYield 54.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.09 g of 2,2-bisfluoromethyl-6-nitro-4-(1,2-dihydro-2-thioxo-1-pyridyl)-2H-1-benzopyran, 0.20 g of methyl iodide and 5 ml of tetrahydrofuran was refluxed for 50 minutes. To the mixture were added 57 mg of cyanamide and 13 mg of sodium hydride (60%) and the mixture was refluxed for 1.5 hours. Methylene chloride was added thereto and the mixture was filtered to remove insoluble materials. The mother liquor was distilled off and the resultant residue was purified using silica gel column chromatography (developing solution, AcOEt:hexane=1:1) to obtain 0.05 g of 4-(2-cyanoimino-1,2-dihydro-1-pyridyl)-2,2-bisfluoromethyl-6-nitro-2H-1-benzopyran represented by the following formula having a melting point of 238-240° C.

Workup

  1. temperaturewas refluxed for 50 minutes
  2. temperaturethe mixture was refluxed for 1.5 hours
  3. filtrationthe mixture was filtered
  4. customto remove insoluble materials
  5. distillationThe mother liquor was distilled off
  6. customthe resultant residue was purified

Sources & evidence

ORD record
ord-a559e8ef5bc14c56aa726dd3d47898a6
Source dataset
uspto-grants-1999_11
Patent number
US05977167

Reaction notes

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