Ethyl Acetate → 7-Amino-4-chloro-6-fluoro-2-methylbenzothiazole

HRID 1419711Notes

Reaction equation

HRID 1419711 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[C:9]([CH3:11])[S:10][C:6]=2[C:5]([N+:12]([O-])=O)=[C:4]([F:15])[CH:3]=1.C(OCC)(=O)C>O.Cl.[Fe]>[NH2:12][C:5]1[C:6]2[S:10][C:9]([CH3:11])=[N:8][C:7]=2[C:2]([Cl:1])=[CH:3][C:4]=1[F:15]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 537041054-Chloro-6-fluoro-2-methyl-7-nitrobenzothiazole

Product 1

HCID 537099237-Amino-4-chloro-6-fluoro-2-methylbenzothiazole

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

6 g of iron powder were added to a suspension of 8 g (32 mmol) of 4-chloro-6-fluoro-2-methyl-7-nitrobenzothiazole in 100 ml of water and 9 ml of concentrated hydrochloric acid, which suspension had been heated to 80° C., after which the mixture was refluxed for 3 hours. 200 ml of ethyl acetate were then added to the reaction mixture. The solid was filtered off. The remaining organic phase was washed with water, dried over magnesium sulfate and finally evaporated down. Yield: 4.5 g.

Workup

  1. temperatureafter which the mixture was refluxed for 3 hours
  2. filtrationThe solid was filtered off
  3. washThe remaining organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customfinally evaporated down

Sources & evidence

ORD record
ord-37de1006222e41ceac0e5112e086f55f
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

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