Methyl iodide → HCID 14973029, compound

HRID 1087180Notes

Reaction equation

HRID 1087180 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[H-].[Na+].[CH3:14]I>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([S:11][CH3:14])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14973030HCID 14973030, compound

Product 1

HCID 14973029HCID 14973029, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-chloro-4-nitrothiophenol (3.3 g) in N,N-dimethylformamide (5 ml) was added dropwise to an ice-cooled mixture of 60% sodium hydride (0.7 g) in N,N-dimethylformamide (10 ml). The mixture was stirred at 0° to 5° C. for 1 hour. To the above mixture was added dropwise methyl iodide (3.7 g) at 5° C. The mixture was stirred at room temperature for 1 hour, poured into ice-water (80 ml), and extracted with toluene. The extract was dried and evaporated. The oily residue was crystallized from a mixture of hexane and ethanol to give crystals of 3-chloro-4-nitrothioanisole (2.8 g).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. extractionextracted with toluene
  4. customThe extract was dried
  5. customevaporated
  6. customThe oily residue was crystallized from a mixture of hexane and ethanol

Sources & evidence

ORD record
ord-d56cd4526cc044ce8f250fb58fc66f13
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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