Bendazac → [(1-Benzyl-1H-indazol-3-yl)oxy]acetyl chloride

HRID 1414162Notes

Reaction equation

HRID 1414162 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][C:19]([OH:21])=O)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>C1C=CC=CC=1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([O:17][CH2:18][C:19]([Cl:24])=[O:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2313BendazacHCID 24386Thionyl Chloride

Product 1

HCID 21486343[(1-Benzyl-1H-indazol-3-yl)oxy]acetyl chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

[(1-BENZYL-1H-indazol-3-yl)-oxy]acetic acid (Bendazac) (50 g) are suspended in benzene (500 ml) and thionyl chloride (15 ml) is added. The solution is stirred under reflux for about half an hour, cooled, concentrated at room temperature under reduced pressure, the oily residue is treated with further benzene and concentrated again to dryness under vacuum. After addition of hexane, the acidic chloride precipitates as lightly coloured crystals. The solution is filtered and washed with hexane. The substance is colourless and shows m.p. 78°-9°. Yield: 90% of the calculated.

Workup

  1. temperatureunder reflux for about half an hour
  2. temperaturecooled
  3. concentrationconcentrated at room temperature under reduced pressure
  4. additionthe oily residue is treated with further benzene
  5. concentrationconcentrated again to dryness under vacuum
  6. additionAfter addition of hexane
  7. customthe acidic chloride precipitates as lightly coloured crystals
  8. filtrationThe solution is filtered
  9. washwashed with hexane

Sources & evidence

ORD record
ord-924798faf7fc4835bb271cf9a2d79154
Source dataset
uspto-grants-1977_01
Patent number
US04001219

Reaction notes

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