3-ethoxycarbonylmethyl-6-fluoro-5-nitro-2(3H)-benzothiazolone → 5-amino-3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazolone

HRID 2413867

Reaction equation

HRID 2413867 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:11]2[CH:12]=[C:13]([N+:17]([O-])=O)[C:14]([F:16])=[CH:15][C:10]=2[S:9][C:8]1=[O:20])=[O:5])[CH3:2]>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:17][C:13]1[C:14]([F:16])=[CH:15][C:10]2[S:9][C:8](=[O:20])[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:11]=2[CH:12]=1

Participants

5

Reactant 1

HCID 140142443-ethoxycarbonylmethyl-6-fluoro-5-nitro-2(3H)-benzothiazolone

Product 1

HCID 140142455-amino-3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazoloneYield 71.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Electrolytic iron powder (0.29 g) was suspended in 5% acetic acid (2 ml), and a solution of 3-ethoxycarbonylmethyl-6-fluoro-5-nitro-2(3H)-benzothiazolone (0.31 g) in acetic acid (1 ml) and ethyl acetate (1 ml) was dropwise added thereto while heating. The resultant mixture was heated under reflux for 3 hours. The reaction mixture was subjected to filtration with celite, and the filtrate was extracted with ethyl acetate. The extract was washed with water and sodium bicarbonate solution, dried and concentrated to give 0.20 g of 5-amino-3-ethoxycarbonylmethyl-6-fluoro-2(3H)-benzothiazolone. m.p., 172.5°-173.5° C.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux for 3 hours
  3. filtrationThe reaction mixture was subjected to filtration with celite
  4. extractionthe filtrate was extracted with ethyl acetate
  5. washThe extract was washed with water and sodium bicarbonate solution
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7a49f3b3f702425d888959464e3b06dc
Source dataset
uspto-grants-1988_01
Patent number
US04720297

Linked notes

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