Dimethylamine → HCID 86722788, compound

HRID 2203398Notes

Reaction equation

HRID 2203398 reaction equation
[CH3:1][N:2]([CH3:10])[S:3]([CH2:6][CH2:7][CH2:8]Cl)(=[O:5])=[O:4].[CH3:11][NH:12][CH3:13].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC#N.O>[CH3:1][N:2]([CH3:10])[S:3]([CH2:6][CH2:7][CH2:8][N:12]([CH3:13])[CH3:11])(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 100353283-chloro-N,N-dimethylpropane-1-sulfonamide

Product 1

HCID 86722788HCID 86722788, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 3-chloro-propane-1-sulfonic acid dimethylamide (0.55 g, 3.00 mmol) in MeCN (5 mL) was treated with dimethylamine (2 M in THF; 10 mL, 20 mmol), potassium carbonate (455 mg, 3.30 mmol) and a catalytic amount of potassium iodide (50 mg, 0.03 mmol). This mixture was heated in a sealed tube at 65° C. for 18 hours, then cooled and diluted with water and extracted into EtOAc. The organic extract was washed with brine then dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a pale brown oil (0.40 g).

Workup

  1. temperaturecooled
  2. extractionextracted into EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialthen dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a38e671ffbb14fedb93ed4df0afd6375
Source dataset
uspto-grants-2016_06
Patent number
US09365577B2

Reaction notes

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