Ethanolamine → HCID 43501950, compound

HRID 548751Notes

Reaction equation

HRID 548751 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].[CH2:13]([CH2:15][NH2:16])[OH:14]>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]([NH:16][CH2:15][CH2:13][OH:14])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 27342732,4-Difluorobenzenesulfonyl Chloride

Product 1

HCID 43501950HCID 43501950, compoundYield 15.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

2,4-Difluorobenzenesulfonyl chloride (4 g, 18.81 mmol) in DCM (10 mL) was added slowly to a solution of ethanolamine (1.25 mL, 20.70 mmol) in DCM (200 mL) and 10% sodium hydroxide solution (200 mL) at 0° C. The reaction was allowed to warm to RT and stirred for 20 hours. The DCM layer was separated and the aqueous re-extracted into DCM (2×50 mL) then the combined organics discarded. The aqueous layer was acidified and extracted into DCM (4×100 mL) the combined organics washed with brine, dried (MgSO4), filtered and reduced in vacuo to give the desired compound as a white solid (0.7 g). 1H NMR δ (CDCl3): 1.75 (s, 1H), 3.17 (q, 2H), 3.72-3.73 (m, 2H), 5.16 (s, 1H), 6.94-7.03 (m, 2H), 7.90-7.97 (m, 1H); m/z 236 (M−H)−

Workup

  1. customThe DCM layer was separated
  2. extractionthe aqueous re-extracted into DCM (2×50 mL)
  3. extractionextracted into DCM (4×100 mL) the combined
  4. washorganics washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-4876c7b8cc6f406d8d6a007d15b81d46
Source dataset
uspto-grants-2011_05
Patent number
US07943607B2

Reaction notes

Loading…