Water → HCID 13960990, compound

HRID 477596Notes

Reaction equation

HRID 477596 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-545b6cd7e4fe4c79b1557fad7be82a57
Source dataset
uspto-grants-1989_12
Patent number
US04888428

Reaction notes

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