4-Toluenesulfonyl chloride → HCID 21273227, compound

HRID 1382779Notes

Reaction equation

HRID 1382779 reaction equation
C(=O)([O-])O.[Na+].[I:6][C:7]1[N:8]=[C:9]([CH3:12])[NH:10][CH:11]=1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C(#N)C>[I:6][C:7]1[N:8]=[C:9]([CH3:12])[N:10]([S:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=2)(=[O:21])=[O:20])[CH:11]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 178433060HCID 178433060, compound

Product 1

HCID 21273227HCID 21273227, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Sodium hydrogen carbonate (9 g) was added to a stirred solution of 4-iodo-2-methyl-1H-imidazole (9.0 g) in acetonitrile (125 ml) followed by a solution of p-toluenesulphonyl chloride (8.3 g) in acetonitrile (50 ml). The resulting mixture was maintained at ca. 40° for 5 h. The reaction mixture was filtered, concentrated in vacuo to ca. 30 ml and n-hexane (ca. 350 ml) was added, precipitating the title compound (7.8 g) as crystals, m.p. 113°-114°. Concentration of the mother liquors (to ca. 50 ml) afforded further title compound (6.1 g), m.p. 112°-114°.

Workup

  1. temperatureThe resulting mixture was maintained at ca. 40° for 5 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo to ca. 30 ml and n-hexane (ca. 350 ml)
  4. additionwas added
  5. customprecipitating the title compound (7.8 g) as crystals, m.p. 113°-114°

Sources & evidence

ORD record
ord-26bd58e4d0bb4eb58e895ed5818823f6
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

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