Diethyl Ether → (s)-2-(4-Nitrophenyl)-1-(2-phenylthiazol-4-yl)ethanamine hydrobromide salt

HRID 424892

Reaction equation

HRID 424892 reaction equation
C(OC(=O)[NH:7][CH:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)[C:9](=O)[CH2:10][Br:11])(C)(C)C.[C:24](=[S:32])([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OCC)C>CC#N>[BrH:11].[N+:20]([C:17]1[CH:16]=[CH:15][C:14]([CH2:13][C@@H:8]([C:9]2[N:31]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[S:32][CH:10]=2)[NH2:7])=[CH:19][CH:18]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 683563ThiobenzamideHCID 76068232[3-Bromo-1-(4-nitro-benzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 66704795(s)-2-(4-Nitrophenyl)-1-(2-phenylthiazol-4-yl)ethanamine hydrobromide saltYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of [3-bromo-1-(4-nitro-benzyl)-2-oxo-propyl]-carbamic acid tert-butyl ester, 37, (1.62 g, 4.17 mmol) and benzothioamide (0.630 g, 4.59 mmol), in CH3CN (5 mL) is refluxed for 24 hours. The reaction mixture is cooled to room temperature and diethyl ether (50 mL) is added to the solution and the precipitate that forms is collected by filtration. The solid is dried under vacuum to afford 1.059 g (63%) of the desired product. ESI+ MS 326 (M+1).

Workup

  1. filtrationthe precipitate that forms is collected by filtration
  2. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-38b08f4bb9f74240907d46880e2bb8b8
Source dataset
uspto-grants-2012_01
Patent number
US08106078B2

Linked notes

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