2-(Methylamino)ethanol → HCID 11485905, compound

HRID 431621Notes

Reaction equation

HRID 431621 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].C(N([CH:12]([CH3:14])[CH3:13])CC)(C)C.[CH3:15][C:16]1[CH:17]=[C:18]([S:22](Cl)(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1>ClCCl>[CH3:1][N:2]([S:22]([C:18]1[CH:19]=[C:12]([CH3:13])[CH:14]=[CH:16][CH:17]=1)(=[O:24])=[O:23])[CH2:3][CH2:4][O:5][S:22]([C:18]1[CH:17]=[C:16]([CH3:15])[CH:21]=[CH:20][CH:19]=1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 81531DiisopropylethylamineHCID 27345953-Methylbenzenesulphonyl chloride

Product 1

HCID 11485905HCID 11485905, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methylaminoethanol (1.0 g, 13 mmol) and diisopropylethylamine (5.8 ml, 33 mmol) in dichloromethane (50 ml) at room temperature was added 3-methylphenylsulfonyl chloride (5.6 g, 29 mmol). The solution was heated to reflux under argon for 12 hours then cooled and partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic phase was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography to afford the title compound (2.5 g, 50%).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux under argon for 12 hours
  3. temperaturethen cooled
  4. custompartitioned between saturated aqueous sodium bicarbonate and dichloromethane
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8e8779aeb178471eac1cbfe3f4e4b3f0
Source dataset
uspto-grants-2003_12
Patent number
US06660751B1

Reaction notes

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