2-(Methylamino)ethanol → 2,4-difluoro-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide

HRID 600557Notes

Reaction equation

HRID 600557 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[CH3:13][NH:14][CH2:15][CH2:16][OH:17]>C(Cl)Cl.[OH-].[Na+]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([N:14]([CH2:15][CH2:16][OH:17])[CH3:13])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 27342732,4-Difluorobenzenesulfonyl Chloride

Product 1

HCID 576631632,4-difluoro-N-(2-hydroxyethyl)-N-methylbenzenesulfonamideYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

2,4-Difluorobenzenesulfonyl chloride (CAS no. 13918-92-8) (4.0 g, 19 mmol) in DCM (10 mL) was added slowly to a solution of 2-(methylamino)ethanol (1.66 mL, 20.7 mmol) in DCM (200 mL) and 10% sodium hydroxide solution (200 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred for 20 hours. The DCM layer was separated and the aqueous re-extracted into DCM (2×50 mL). The combined organic extracts were washed with brine (200 mL), dried (MgSO4), filtered and evaporated under reduced pressure to afford the product (4.7 g, 98%). 1H NMR δ (400 MHz, CDCl3): 1.98 (t, 1H), 2.94 (s, 3H), 3.32 (t, 2H), 3.79 (q, 2H), 6.94-7.03 (m, 2H), 7.89-7.95 (m, 1H).

Workup

  1. customThe DCM layer was separated
  2. extractionthe aqueous re-extracted into DCM (2×50 mL)
  3. washThe combined organic extracts were washed with brine (200 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-621ad555fe5a4eb7b5c7660ef881a709
Source dataset
uspto-grants-2011_03
Patent number
US07902200B2

Reaction notes

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