2-(Methylamino)ethanol → HCID 86722314, compound

HRID 874825Notes

Reaction equation

HRID 874825 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[N:6]([C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)=[C:7]=[O:8]>C(Cl)Cl>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[C:7](=[O:8])[NH:6][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 28045423138-53-6

Product 1

HCID 86722314HCID 86722314, compoundYield 112.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of N-methylethanolamine (0.600 g, 7.99 mmol) in DCM (80 mL) was added methyl 4-isocyanatobenzoate (1.56 g, 8.79 mmol). After 20 minutes the coolant was removed and the reaction mixture was stirred for 2 hours. The solvent was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0 to 100% ethyl acetate/iso-hexane to afford the title compound (2.26 g, 112%).

Workup

  1. customAfter 20 minutes the coolant was removed
  2. customThe solvent was evaporated at reduced pressure
  3. customthe residue was purified by flash column chromatography
  4. washeluting with 0 to 100% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-66ea7629106a431fa77066cc698c49fe
Source dataset
uspto-grants-2015_03
Patent number
US08980913B2

Reaction notes

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