Sodium Carbonate → HCID 178433557, compound

HRID 1670537Notes

Reaction equation

HRID 1670537 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][C:7]1[NH:8][CH:9]=[CH:10][N:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>S(Cl)(Cl)=O>[CH3:6][C:7]1[NH:8][CH:9]=[C:10]([S:2]([Cl:1])(=[O:5])=[O:3])[N:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 127492-MethylimidazoleHCID 24638Chlorosulfonic acid

Product 1

HCID 178433557HCID 178433557, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
150 °C

Procedure

Carefully add chlorosulfonic acid (30 mL) to neat 2-methylimidazole (5 g, 60.9 mmol). Heat the mixture at 150° C. for 3 h and cool to room temperature. Add thionyl chloride (10 mL), heat at 100° C. for 3 h and cool to room temperature. Carefully pour the mixture into ice. Slowly add solid sodium carbonate to neutralize the solution. Filter the precipitate formed and wash with water. Dry the solid under high vacuum overnight at 45° C. to give the desired intermediate (4.38 g, 40%). MS (ES+) m/z: 181 (M+H)+.

Workup

  1. temperaturecool to room temperature
  2. temperaturecool to room temperature
  3. additionCarefully pour the mixture into ice
  4. filtrationFilter the precipitate
  5. customformed
  6. washwash with water
  7. customDry the solid under high vacuum overnight at 45° C.

Sources & evidence

ORD record
ord-9ef7d026e5f84a4bb1a2e141502b06f6
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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