Ethanolamine → HCID 68325563, compound

HRID 2403315Notes

Reaction equation

HRID 2403315 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][O:9]2)=[CH:4][C:3]=1[Cl:11].[NH2:12][CH2:13][CH2:14][OH:15].CCOC(C)=O.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:9])[CH2:10][NH:12][CH2:13][CH2:14][OH:15])=[CH:4][C:3]=1[Cl:11]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 21939870Tetrahydrofuran ethyl acetateHCID 86671405HCID 86671405, compound

Product 1

HCID 68325563HCID 68325563, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-2-(4-bromo-3-chloro-phenyl)-oxirane (15.2 g) in THF (40 ml) was added 2-aminoethanol (35.1 ml) and the mixture was stirred at room temperature for 7 hours. The reaction mixture was then poured into EtOAc/THF (1:1) and washed with saturated brine. The organic layer was separated and was then dried over Na2SO4 and concentrated in vacuo to afford (RS)-1-(4-bromo-3-chlorophenyl)-2-(2-hydroxyethylamino)ethanol (19.0 g) as a yellow oil which was used in the next step without further purification. MS (ISP): 298.1 ([{81Br37Cl}M+H]+), 296.0 ([{81Br35Cl or 79Br37Cl}M+H]+), 293.9 ([{79Br35Cl}M+H]).

Workup

  1. washwashed with saturated brine
  2. customThe organic layer was separated
  3. dry with materialwas then dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7b5f73edcb546c5ab9b5716e8f22815
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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