Methyl iodide → HCID 54276332, compound

HRID 1656921Notes

Reaction equation

HRID 1656921 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[C:14]([N+:20]([O-:22])=[O:21])[CH2:15][S:16][CH2:17][CH:18]=[CH2:19])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH3:27]I>CN(C)C=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][N:11]([CH3:27])[C:10]2=[C:14]([N+:20]([O-:22])=[O:21])[CH2:15][S:16][CH2:17][CH:18]=[CH2:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86747327HCID 86747327, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54276332HCID 54276332, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.5 g of 1-(6-chloro-3-pyridylmethyl)-2-(1-nitro-2-allylthioethylidene)imidazolidine was dissolved in 10 ml of N,N-dimethylformamide, and 0.06 g of sodium hydride (60% oil suspension) was then gradually added thereto at room temperature. The resultant reaction liquor was continuously stirred for about 15 minutes until the generation of hydrogen gas stopped, and thereafter 0.18 g of methyl iodide was gradually added dropwise to the reaction liquor. The reaction liquor was further continuously stirred for 2 hours at room temperature, and the solvent was then distilled off under reduced pressure to obtain a residue. The residue thus obtained was purified by silica gel column chromatography (eluting solution: ethyl acetate/methanol =2/1) to obtain 0.26 g of the desired compound (Compound No. 63) having a refractive index of nD39.0 =1.6205.

Workup

  1. customat room temperature
  2. customThe resultant reaction liquor
  3. distillationthe solvent was then distilled off under reduced pressure
  4. customto obtain a residue
  5. customThe residue thus obtained
  6. customwas purified by silica gel column chromatography (eluting solution: ethyl acetate/methanol =2/1)

Sources & evidence

ORD record
ord-3801caa4ba06448aafe720e6d88b70d6
Source dataset
uspto-grants-1993_10
Patent number
US05256674

Reaction notes

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