Hydroxide → HCID 15617817, compound

HRID 1194590Notes

Reaction equation

HRID 1194590 reaction equation
[CH:1]([NH:4][NH:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)([CH3:3])[CH3:2].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-]>C(Cl)CCl>[C:16]([N:4]([CH:1]([CH3:3])[CH3:2])[NH:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 961HydroxideHCID 7412Benzoyl chlorideHCID 15617779HCID 15617779, compound

Product 1

HCID 15617817HCID 15617817, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3,4-dichlorobenzoic acid, 2-isopropylhydrazide (0.98 g, 0.004 mole) and benzoyl chloride (0.56 g, 0.004 mole) is stirred overnight in 1.2 mL of ethylene dichloride and 6.5 mL of 10% soldium hydroxide. The organic phase is removed and the aqueous mixture is extracted with 25 mL of ethylene dichloride. The organic extracts are combined and concentrated to a yellow oil which is taken up in hot isopropyl alcohol. Cooling the alcohol solution causes precipitation of the title compound as a white crystalline product, which is collected by filtration and has a mp of 157° C.

Workup

  1. customThe organic phase is removed
  2. extractionthe aqueous mixture is extracted with 25 mL of ethylene dichloride
  3. concentrationconcentrated to a yellow oil which
  4. temperatureCooling the alcohol solution
  5. customprecipitation of the title compound as a white crystalline product, which
  6. filtrationis collected by filtration

Sources & evidence

ORD record
ord-38e543949e3244f1bfc2218cb8e9ecbc
Source dataset
uspto-grants-1989_03
Patent number
US04814349

Reaction notes

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