2-(Methylamino)ethanol → N-(2-Hydroxyethyl)-4-methoxy-N,2,6-trimethylbenzenesulfonamide

HRID 2388655Notes

Reaction equation

HRID 2388655 reaction equation
C(N(CC)CC)C.[CH3:8][NH:9][CH2:10][CH2:11][OH:12].[CH3:13][O:14][C:15]1[CH:20]=[C:19]([CH3:21])[C:18]([S:22](Cl)(=[O:24])=[O:23])=[C:17]([CH3:26])[CH:16]=1>>[OH:12][CH2:11][CH2:10][N:9]([CH3:8])[S:22]([C:18]1[C:19]([CH3:21])=[CH:20][C:15]([O:14][CH3:13])=[CH:16][C:17]=1[CH3:26])(=[O:24])=[O:23]

Participants

4

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 159174964-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Product 1

HCID 51712110N-(2-Hydroxyethyl)-4-methoxy-N,2,6-trimethylbenzenesulfonamide

Conditions

Temperature
0 °C

Procedure

Triethylamine (213 ml, 1,512.5 mmol) was added to a solution of 2-(methylamino)ethanol (53.5 ml, 665.5 mmol) in MC (1,250 ml) and the mixture was cooled to 0° C. A solution of 4-methoxy-2,6-dimethylbenzene-1-sulfonyl chloride (142 g, 605 mmol) [see AC5, Stage 1] in MC (750 ml) was then slowly added dropwise. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was then washed with aqueous 0.5 M HCl (800 ml) and water (2×1,000 ml). The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. Purification was carried out by chromatography on silica gel (heptane/ethyl acetate 1:1). The yield was 116.3 g (70%).

Workup

  1. washThe organic phase was then washed with aqueous 0.5 M HCl (800 ml) and water (2×1,000 ml)
  2. dry with materialThe combined organic phases were dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-1fdd4925d7354cdbbb4e502316bc8f32
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

Loading…