Water → HCID 13960990, compound

HRID 2232011Notes

Reaction equation

HRID 2232011 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

A suspension of iron powder (0.77 g) in 5% aqueous acetic acid (1.5 ml) was heated at 80° C., and 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, followed by heating under reflux at 60° to 80° C. for 3 hours. After cooling, water and ethyl acetate were added to the resultant mixture, followed by filtration. The filtrate was extracted with ethyl acetate, and the extract was washed with water and sodium bicarbonate solution, dried and concentrated to give 5-amino-3-allyl-6-fluoro-2(3H)-benzothiazolone (0.60 g). nD26.0 1.6236.

Workup

  1. temperatureby heating
  2. temperatureunder reflux at 60° to 80° C. for 3 hours
  3. temperatureAfter cooling
  4. filtrationfollowed by filtration
  5. extractionThe filtrate was extracted with ethyl acetate
  6. washthe extract was washed with water and sodium bicarbonate solution
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-75fce475dc29441ea27b551de8b40b62
Source dataset
uspto-grants-1988_11
Patent number
US04786310

Reaction notes

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