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

HRID 705543Notes

Reaction equation

HRID 705543 reaction equation
[Br:1][CH2:2][C:3](=O)[C@@H:4]([NH:15]C(=O)OC(C)(C)C)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[C:24]([NH2:32])(=[S:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(OCC)C>CC#N>[BrH:1].[N+:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C@@H:4]([C:3]2[N:32]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[S:31][CH:2]=2)[NH2:15])=[CH:11][CH:10]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 683563ThiobenzamideHCID 53778469(S)-tert-Butyl (4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-yl)carbamate

Product 1

HCID 66704795(s)-2-(4-Nitrophenyl)-1-(2-phenylthiazol-4-yl)ethanamine hydrobromide saltYield 67%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (S)-tert-butyl 4-bromo-1-(4-nitrophenyl)-3-oxobutan-2-ylcarbamate, 7, (1.62 g, 4.17 mmol) and thiobenzamide (0.63 g, 4.60 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. The precipitate which forms is collected by filtration. The solid is dried under vacuum to afford 1.2 g (67% yield) of the desired product. LC/MS ESI+ 326 (M+1).

Workup

  1. temperatureis refluxed for 24 hours
  2. filtrationThe precipitate which forms is collected by filtration
  3. customThe solid is dried under vacuum

Sources & evidence

ORD record
ord-1d8e54e8afff4b2a8b3506f2a8ab8a53
Source dataset
uspto-grants-2015_11
Patent number
US09174950B2

Reaction notes

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