Triethylamine → 3-chloro-N,N-dimethylpropane-1-sulfonamide

HRID 2262266Notes

Reaction equation

HRID 2262266 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(N(CC)CC)C.[Cl:12][CH2:13][CH2:14][CH2:15][S:16](Cl)(=[O:18])=[O:17]>ClCCl>[CH3:2][N:3]([CH3:4])[S:16]([CH2:15][CH2:14][CH2:13][Cl:12])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 154103-Chloropropanesulphonyl chloride

Product 1

HCID 100353283-chloro-N,N-dimethylpropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of dimethylamine hydrochloride (1.38 g) in dichloromethane (20 mL) was added triethylamine (2.52 mL) and then 3-chloropropanesulfonyl chloride (0.69 mL) and the reaction was stirred at room temperature for 16 h. The reaction was quenched with water (20 mL) and extracted into dichloromethane (2×30 mL). The combined organics were washed with 1 M aqueous hydrochloric acid solution (40 mL) then saturated aqueous sodium hydrogen carbonate solution, dried (MgSO4) and reduced in vacuo to give 3-chloro-propane-1-sulfonic acid dimethylamide as a yellow solid.

Workup

  1. customThe reaction was quenched with water (20 mL)
  2. extractionextracted into dichloromethane (2×30 mL)
  3. washThe combined organics were washed with 1 M aqueous hydrochloric acid solution (40 mL)
  4. dry with materialsaturated aqueous sodium hydrogen carbonate solution, dried (MgSO4)

Sources & evidence

ORD record
ord-576f09ce2b924909977a3ecfa407c544
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

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