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

HRID 2193888Notes

Reaction equation

HRID 2193888 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-c48243c996514197babc1f469156e866
Source dataset
uspto-grants-2012_12
Patent number
US08329916B2

Reaction notes

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