Dimethylamine → HCID 14774741, compound

HRID 902658Notes

Reaction equation

HRID 902658 reaction equation
[CH3:1][NH:2][CH3:3].[CH3:4][O:5][C:6]1[CH:7]=[C:8]([S:12](Cl)(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1.N1C=CC=CC=1.O>C1COCC1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([S:12]([N:2]([CH3:3])[CH3:1])(=[O:14])=[O:13])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 1049PyridineHCID 27375043-Methoxybenzenesulfonyl chloride

Product 1

HCID 14774741HCID 14774741, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dimethylamine (40% in H2O, 1 mL) was added to a solution of 3-methoxybenzenesulfonyl chloride (0.50 g, 2.4 mmol) and pyridine (1 mL) in THF (5 mL). The reaction mixture was allowed to stir at rt for 48 h, then was poured into H2O and extracted with EtOAc. The organic extracts were washed with brine, dried (MgSO4), filtered and concentrated to give an oil which was chromatographed (10-80% EtOAc in hexane) to give 0.400 g (76%) of the title compound. MS (ESI) 216 (M+H+).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oil which
  7. customwas chromatographed (10-80% EtOAc in hexane)

Sources & evidence

ORD record
ord-28e94250bad646188947e6e8f8528eb0
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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