Diethyl Ether → (S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamine

HRID 1437844Notes

Reaction equation

HRID 1437844 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[CH2:24][C:25](=O)[CH2:26][CH3:27].C(OCC)C>CC#N>[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 57943187(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamineYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of [2-(4-nitrophenyl)-1-(S)-thiocarbamoylethyl]-carbamic acid tert-butyl ester, 2, (0.245 g, 0.753 mmol), 1-bromo-2-butanone (0.125 g, 0.828 mmol) in CH3CN (5 mL) is refluxed 3 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. The solid is dried under vacuum to afford 0.242 g (90% yield) of the desired product. ESI+MS 278 (M+1).

Workup

  1. temperatureis refluxed 3 hours
  2. customthe precipitate which forms is removed by filtration
  3. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-b0e32ebe83af4e618744ef5c8dfc5618
Source dataset
uspto-grants-2009_11
Patent number
US07622593B2

Reaction notes

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