2-Methoxyethylamine → 2-(4-Bromo-1H-pyrazol-1-yl)-N-(2-methoxyethyl)ethanamine

HRID 84369Notes

Reaction equation

HRID 84369 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[Br:6][C:7]1[CH:8]=[N:9][N:10]([CH2:12][CH2:13]Cl)[CH:11]=1>CS(C)=O.CCOC(C)=O>[Br:6][C:7]1[CH:8]=[N:9][N:10]([CH2:12][CH2:13][NH:5][CH2:4][CH2:3][O:2][CH3:1])[CH:11]=1

Participants

5

Reactant 2

HCID 80182-MethoxyethylamineHCID 518920744-Bromo-1-(2-chloroethyl)-1H-pyrazole

Product 1

HCID 625656882-(4-Bromo-1H-pyrazol-1-yl)-N-(2-methoxyethyl)ethanamine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-methoxyethanamine (8.9 mL, 102.06 mmol) and chloride 75 (7.13 g, 34.02 mmol) in DMSO (20 mL) was heated at 60° C. 5 h. The mixture was then cooled to room temperature, diluted with EtOAc, washed with aqueous sodium bicarbonate, water and brine.

Workup

  1. custom5 h
  2. washwashed with aqueous sodium bicarbonate, water and brine

Sources & evidence

ORD record
ord-d2b70bd9f5b946e39495ccc7c33c597b
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Reaction notes

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