Isoamyl Nitrite → 7-Fluorobenzo[d]thiazole
Reaction equation
[F:1][C:2]1[C:10]2[S:9][C:8](N)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.N(OCCC(C)C)=O>C1COCC1>[F:1][C:2]1[C:10]2[S:9][CH:8]=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 7-fluorobenzo[d]thiazol-2-amine 25C (1 g, 5.95 mmol) in THF (10 mL) was added isoamyl nitrite (1.51 g, 12.9 mmol) at room temperature. After refluxing for 3 hr, the reaction mixture was then allowed to cool to room temperature and poured into ice water (50 mL), and then extracted with EtOAc. The organic extract was washed with water and brine, dried and evaporated. The residue was chromatographed on silica gel to get the 7-fluorobenzo[d]thiazole as colorless oil. LC-MS: m/z 154.2 (M+H)+
Workup
- temperatureAfter refluxing for 3 hr
- extractionextracted with EtOAc
- extractionThe organic extract
- washwas washed with water and brine
- customdried
- customevaporated
- customThe residue was chromatographed on silica gel
Sources & evidence
- ORD record
- ord-96389c24297e4bccaedb277c2ae87532
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108921B2
Reaction notes
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