Hydrochloric Acid → 2-Chloro-6-fluorobenzothiazole

HRID 707416Notes

Reaction equation

HRID 707416 reaction equation
N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.N(OC(C)(C)C)=O.[ClH:19]>C(#N)C.[Cu](Cl)Cl>[Cl:19][C:2]1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 3199542-Amino-6-fluorobenzothiazole

Product 1

HCID 20498702-Chloro-6-fluorobenzothiazoleYield 83%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a round bottomed flask was added 2-amino-6-fluorobenzothiazole (1.0017 g, 5.96 mmol, Sigma-Aldrich Chemical Company, Inc.), copper (II) chloride (1.201 g, 8.93 mmol, Sigma-Aldrich Chemical Company, Inc.), and tert-butyl nitrite (1.063 ml, 8.93 mmol, Acros Organics) in ACN and was heated to 65° C. for 2 hours. The reaction mixture was diluted with 1N HCl and extracted with EtOAc. The organic extract was washed with water, satd NaCl, dried over MgSO4, filtered and concentrated in vacuo to give the title compound (0.9249 g, 4.93 mmol, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm s 7.45 (td, J=9.10, 2.74 Hz, 1 H) 7.97-8.07 (m, 2 H)

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e2895b4ddf5d41b49f76c5fca77aa582
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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