Triethylamine → HCID 13161805, compound

HRID 1488223Notes

Reaction equation

HRID 1488223 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[CH3:7][N:8]([CH3:13])[S:9](Cl)(=[O:11])=[O:10].C(N(CC)CC)C>ClCCl>[CH3:7][N:8]([CH3:13])[S:9]([N:3]1[CH:4]=[CH:5][N:6]=[C:2]1[CH3:1])(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 127492-MethylimidazoleHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 13161805HCID 13161805, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-1H-imidazole (10 g, 121.8 mmol) in dichloromethane (100 mL) was added N,N-dimethylsulfamoyl chloride (14.4 mL, 133.7 mmol) and triethylamine (34 mL, 244.1 mmol). The reaction mixture was stirred overnight at room temperature, then quenched with 10 mL of water and extracted with 1×50 mL of DCM. The organic layer was washed with 2×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:2) as the eluent to furnish 20 g (87%) of the title compound as a yellow oil.

Workup

  1. customquenched with 10 mL of water
  2. extractionextracted with 1×50 mL of DCM
  3. washThe organic layer was washed with 2×20 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1:2) as the eluent

Sources & evidence

ORD record
ord-4046cf7fcb874be086352839ab1d9ee4
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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