3-Chloropropanesulphonyl chloride → HCID 63362723, compound

HRID 408593

Reaction equation

HRID 408593 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[CH2:6][NH2:7].[Cl:14][CH2:15][CH2:16][CH2:17][S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:5]=1[CH2:6][NH:7][S:18]([CH2:17][CH2:16][CH2:15][Cl:14])(=[O:20])=[O:19]

Participants

4

Reactant 2

HCID 154103-Chloropropanesulphonyl chlorideHCID 30843432,4-Dimethoxybenzylamine hydrochloride

Product 1

HCID 63362723HCID 63362723, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
20 °C

Procedure

To a solution of 2,4-dimethoxy-benzylamine hydrochloride (1 eq.) and TEA (2 eq.) in DCM was added dropwise at 0° C. a solution of 3-chloro-propane-1-sulfonyl chloride (1 eq.) in DCM. The reaction was stirred at 20° C. for 20 h. The crude was diluted with DCM, washed twice with water, twice with aqueous HCl (0.1N) and twice with a saturated aqueous solution of NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 100/0 to 20/80) to afford 3-chloro-propane-1-sulfonic acid 2,4-dimethoxy-benzylamide.

Workup

  1. washwashed twice with water, twice with aqueous HCl (0.1N) and twice with a saturated aqueous solution of NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 100/0 to 20/80)

Sources & evidence

ORD record
ord-e4ec7a6c826a4b9f8a59e6093972de0c
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Linked notes

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