Isoamyl Nitrite → 7-Fluorobenzo[d]thiazole

HRID 2202367Notes

Reaction equation

HRID 2202367 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-5271db6a91bd4fdb90eb7dfaa57f86f1
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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