2-(Methylamino)ethanol → HCID 86625993, compound

HRID 1992353Notes

Reaction equation

HRID 1992353 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[CH3:13][NH:14][CH2:15][CH2:16][OH:17].C(N(CC)CC)C>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:14]([CH3:13])[CH2:15][CH:16]=[O:17])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 8471TriethylamineHCID 394974-Cyanobenzenesulfonyl chloride

Product 1

HCID 86625993HCID 86625993, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Cyanobenzenesulfonyl chloride (6 g, 0.0297 mol) in 50 ml of dry DCM was added at 0° C. to a solution of N-methylethanolamine (2.67 g, 0.0356 mol) and triethylamine (7.49 g, 0.0742 mol) in dry dichloromethane (75 ml) under nitrogen atmosphere and stirred at RT for 2 h. The reaction mixture was quenched with water and extracted with dichloromethane. Organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure afforded crude product as solid. This solid was then washed with petroleum ether (three times) and dried under vacuum to give the sub-title compound (5.18 g) as white solid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. washOrganic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporation under reduced pressure
  6. customafforded crude product as solid
  7. washThis solid was then washed with petroleum ether (three times)
  8. customdried under vacuum

Sources & evidence

ORD record
ord-4458a6a5dce74ec3803d3be6dd451b09
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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