Isoamyl Nitrite → 7-Fluorobenzo[d]thiazole

HRID 514831Notes

Reaction equation

HRID 514831 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]=1

Participants

4

Reactant 2

HCID 8053Isoamyl NitriteHCID 148922457-Fluoro-1,3-benzothiazol-2-amine

Product 1

HCID 232854367-Fluorobenzo[d]thiazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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

  1. temperatureAfter refluxing for 3 hr
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with water and brine
  5. customdried
  6. customevaporated
  7. 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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