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

HRID 1930530Notes

Reaction equation

HRID 1930530 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, 2, (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 which 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 which forms is collected by filtration
  2. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-b2157f09e82844099b1f3b22f8db85ef
Source dataset
uspto-grants-2012_05
Patent number
US08188125B2

Reaction notes

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