Water → HCID 13960990, compound

HRID 2413866Notes

Reaction equation

HRID 2413866 reaction equation
[CH2:1]([N:4]1[C:8]2[CH:9]=[C:10]([N+:14]([O-])=O)[C:11]([F:13])=[CH:12][C:7]=2[S:6][C:5]1=[O:17])[CH:2]=[CH2:3].O>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:14][C:10]1[C:11]([F:13])=[CH:12][C:7]2[S:6][C:5](=[O:17])[N:4]([CH2:1][CH:2]=[CH2:3])[C:8]=2[CH:9]=1

Participants

6

Reactant 2

HCID 962WaterHCID 139609816-Fluoro-5-nitro-3-(prop-2-en-1-yl)-1,3-benzothiazol-2(3H)-one

Product 1

HCID 13960990HCID 13960990, compoundYield 97.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

Electrolytic iron powder (0.77 g) was suspended in 5% acetic acid (1.5 ml), and the suspension was heated to 80° C. A solution of 3-allyl-6-fluoro-5-nitro-2(3H)-benzothiazolone (0.70 g) in acetic acid (2.8 ml) and ethyl acetate (2.8 ml) was added thereto. The resultant mixture was heated under reflux at a temperature of 60° to 80° C. for 3 hours. After being allowed to cool, water and ethyl acetate were added thereto, the precipitate was collected by filtration, and the filtrate was extracted with ethyl acetate. The extract was washed with water and sodium bicarbonate solution, dried and concentrated to give 0.60 g of 5-amino-3-allyl-6-fluoro-2(3H)-benzothiazolone. nD26.0 1.6236.

Workup

  1. temperatureunder reflux at a temperature of 60° to 80° C. for 3 hours
  2. temperatureto cool
  3. filtrationthe precipitate was collected by filtration
  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-7d6f1d7a229a46ea846c6bdef64af912
Source dataset
uspto-grants-1988_01
Patent number
US04720297

Reaction notes

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