2-(Methylamino)ethanol → 4-Formyl-N-(2-hydroxyethyl)-N-methylbenzenesulfonamide

HRID 874828Notes

Reaction equation

HRID 874828 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].C(N(CC)CC)C.[CH:13]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)=[O:14]>C(Cl)Cl>[CH:13]([C:15]1[CH:16]=[CH:17][C:18]([S:21]([N:2]([CH2:3][CH2:4][OH:5])[CH3:1])(=[O:23])=[O:22])=[CH:19][CH:20]=1)=[O:14]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 27592104-Formylbenzene-1-sulfonyl chloride

Product 1

HCID 867223174-Formyl-N-(2-hydroxyethyl)-N-methylbenzenesulfonamideYield 92.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of 2-(methylamino)ethanol (0.196 mL, 2.44 mmol) and triethylamine (0.407 mL, 2.93 mmol) in DCM (10 mL) was added 4-formylbenzenesulfonyl chloride (0.500 g, 2.44 mmol). The reaction mixture was warmed slowly to RT and stirred at RT for 80 hours. The reaction mixture was diluted with DCM and was washed with 10% aqueous potassium hydrogen sulfate and dried (magnesium sulfate). The mixture filtered and the solvent evaporated at reduced pressure to afford the title compound (0.548 g, 92%).

Workup

  1. washwas washed with 10% aqueous potassium hydrogen sulfate
  2. dry with materialdried (magnesium sulfate)
  3. filtrationThe mixture filtered
  4. customthe solvent evaporated at reduced pressure

Sources & evidence

ORD record
ord-196c8d035891413eac0aea5ba63f1740
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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