Diethyl Ether → 1-(S)-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl amine hydrobromide

HRID 1714507Notes

Reaction equation

HRID 1714507 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:19](=[S:21])[NH2:20])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(C)(C)C.[Br:23][CH2:24][C:25](=O)[CH2:26][CH3:27].C(OCC)C>CC#N>[BrH:23].[CH2:26]([C:25]1[N:20]=[C:19]([C@@H:8]([NH2:7])[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)[S:21][CH:24]=1)[CH3:27]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 131561-Bromo-2-butanoneHCID 57943188[2-(4-nitrophenyl)-1-(S)-thiocarbamoylethyl]carbamic acid tert-butyl ester

Product 1

HCID 666949351-(S)-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl amine hydrobromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of [2-(4-nitrophenyl)-1-(S)-thiocarbamoylethyl]-carbamic acid tert-butyl ester, 2, (10 g, 30.7 mmol) and 1-bromo-2-butanone (90%, 3.8 mL, 33.8 mmol) in CH3CN (500 mL) is refluxed for 18 hours. The reaction mixture is cooled to room temperature and diethyl ether is added to the solution and the precipitate which forms is removed by filtration to afford 7.47 g of the desired product. ESI+ MS 278 (M+1).

Workup

  1. temperatureis refluxed for 18 hours
  2. customthe precipitate which forms is removed by filtration

Sources & evidence

ORD record
ord-ada6436259e043908e031066f8fc0c31
Source dataset
uspto-grants-2010_09
Patent number
US07795444B2

Reaction notes

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