Acetonitrile → 5-Bromo-4-(trifluoromethyl)-1,3-thiazol-2-amine
Reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1[N:4]=[C:5]([NH2:8])[S:6][CH:7]=1.C(#N)C.[Br:14]N1C(=O)CCC1=O>>[Br:14][C:7]1[S:6][C:5]([NH2:8])=[N:4][C:3]=1[C:2]([F:10])([F:9])[F:1]Participants
4
Conditions
- Temperature
- 60 °C
Procedure
To a 250 mL round-bottomed flask were added 4-(trifluoromethyl)thiazol-2-amine (6 g, 36 mmol), ACN (90 mL, 1723 mmol), and N-bromosuccinimide (4 mL, 43 mmol). The solution was stirred at 60° C. for 3 hours. The reaction was cooled, and the solvent was removed in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of (5%→50% EtOAc in hexane) to provide 5-bromo-4-(trifluoromethyl)thiazol-2-amine (8.1 g, 90% yield), m/z (%): 248.2 (100%, M++H).
Workup
- temperatureThe reaction was cooled
- customthe solvent was removed in vacuo
- customchromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
- washeluting with a gradient of (5%→50% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-f37b60ee8c1a46b0bfe699d67ce5cb73
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514566B2
Reaction notes
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