Sodium hydride → HCID 19432932, compound

HRID 1736404Notes

Reaction equation

HRID 1736404 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[S:13]([CH2:15][CH2:16][CH2:17][OH:18])=[O:14].[CH3:19][O:20][CH:21]([O:32][CH3:33])[C:22]1[CH:27]=[C:26](Cl)[CH:25]=[CH:24][C:23]=1[N+:29]([O-:31])=[O:30].[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[S:13]([CH2:15][CH2:16][CH2:17][O:18][C:26]1[CH:25]=[CH:24][C:23]([N+:29]([O-:31])=[O:30])=[C:22]([CH:21]([O:20][CH3:19])[O:32][CH3:33])[CH:27]=1)=[O:14]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 35700934-Chloro-2-(dimethoxymethyl)-1-nitrobenzeneHCID 11043651HCID 11043651, compound

Product 1

HCID 19432932HCID 19432932, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 50 ml of dimethylformamide were added 2.9 g of 3-[1-(2-methylphenyl)-2-imidazolylsulfinyl]propanol and 3.4 g of 5-chloro-2-nitro-benzaldehyde dimethylacetal. To the mixture being stirred was added 0.75 g of 60% sodium hydride slowly. The mixture was stirred at 60° C. overnight. Thereto was added an aqueous solution saturated with ammonium chloride. The reaction mixture was concentrated. The residue was extracted with ethyl acetate. The extract was washed with water and an aqueous solution saturated with sodium chloride, dried with magnesium sulfate, and subjected to distillation to remove ethyl acetate. The residue was purified by a silica gel column chromatography (eluant: dichloromethane/methanol=1/0→50/1) to obtain 3.3 g of 1-(2-methylphenyl)-2-[3-(3-dimethoxymethyl-4-nitrophenoxy)propylsulfinyl]imidazole as a light yellow oil.

Workup

  1. stirringThe mixture was stirred at 60° C. overnight
  2. concentrationThe reaction mixture was concentrated
  3. extractionThe residue was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialan aqueous solution saturated with sodium chloride, dried with magnesium sulfate
  6. distillationsubjected to distillation
  7. customto remove ethyl acetate
  8. customThe residue was purified by a silica gel column chromatography (eluant: dichloromethane/methanol=1/0→50/1)

Sources & evidence

ORD record
ord-b6412b6ecf0048da998884803a49f264
Source dataset
uspto-grants-1996_07
Patent number
US05541198

Reaction notes

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