2,4-Dichloro-6-fluoro-7-nitrobenzothiazole → 7-Amino-2,4-dichloro-6-fluorobenzothiazole

HRID 21725Notes

Reaction equation

HRID 21725 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[C:10]([N+:11]([O-])=O)=[C:9]([F:14])[CH:8]=[C:7]([Cl:15])[C:5]=2[N:6]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:11][C:10]1[C:4]2[S:3][C:2]([Cl:1])=[N:6][C:5]=2[C:7]([Cl:15])=[CH:8][C:9]=1[F:14]

Participants

5

Reactant 1

HCID 199334652,4-Dichloro-6-fluoro-7-nitrobenzothiazole

Product 1

HCID 199334577-Amino-2,4-dichloro-6-fluorobenzothiazole

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5 g Iron powder was added to 40 ml 5% aqueous acetic acid. The mixture was heated to reflux and a solution of 5 g 2,4-dichloro-6-fluoro-7-nitrobenzothiazole in 40 ml acetic acid and 40 ml ethyl acetate was added. The mixture was heated for 2 hours under reflux and after cooling the mixture was filtered over celite, the phases separated and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed with aqueous sodium hydrogen carbonate and water and dried with magnesium sulfate. Yield: 4.3 g=97% of theory m.p.: 173° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureThe mixture was heated for 2 hours
  4. temperatureunder reflux
  5. temperatureafter cooling the mixture
  6. filtrationwas filtered over celite
  7. customthe phases separated
  8. extractionthe aqueous phase extracted with ethyl acetate
  9. washThe combined organic phases were washed with aqueous sodium hydrogen carbonate and water
  10. dry with materialdried with magnesium sulfate

Sources & evidence

ORD record
ord-85822b54c9224dcdb1b547c04bcbde94
Source dataset
uspto-grants-1995_06
Patent number
US05424443

Reaction notes

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