Benzene → HCID 12912153, compound

HRID 614960Notes

Reaction equation

HRID 614960 reaction equation
C1C=CC=CC=1.[CH3:7][N:8]1[C:12]([OH:13])=[C:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C:10]([CH3:24])=[N:9]1.C(N(CC)CC)C.[C:32](Cl)(=[O:44])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>CCOCC>[CH3:7][N:8]1[C:12]([O:13][C:32](=[O:44])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[C:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C:10]([CH3:24])=[N:9]1

Participants

6

Reactant 4

HCID 241Benzene2×HCID 8166Dodecanoyl chlorideHCID 8471TriethylamineHCID 178434070HCID 178434070, compound

Product 1

HCID 12912153HCID 12912153, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In 10 ml. of benzene is dissolved 0.285 g. of 1,3-dimethyl-4-(2,4-dichlorobenzoyl)-5-hydroxypyrazole and then 0.2 ml. of triethylamine is added thereto. Under ice-cooling, a solution of 0.27 g. of lauroyl chloride in 5 ml. of benzene is added dropwise thereto. After completion of the dropwise addition, the resulting mixture is stirred at room temperature for 19 hours. After completion of the reaction, ether is added to the reaction mixture, which is then washed successively with water, 1N HCl, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride. Then, the reaction mixture is dried over anhydrous sodium sulfate and the solvent is distilled off from the reaction mixture. The resulting residue is recrystallized from n-hexane under cooling with dry-ice to give 0.46 g. of the desired product as white crystals melting at 56° C. Yield 98.0%.

Workup

  1. temperatureUnder ice-cooling
  2. additionAfter completion of the dropwise addition
  3. additionis added to the reaction mixture, which
  4. washis then washed successively with water, 1N HCl
  5. dry with materialThen, the reaction mixture is dried over anhydrous sodium sulfate
  6. distillationthe solvent is distilled off from the reaction mixture
  7. customThe resulting residue is recrystallized from n-hexane
  8. temperatureunder cooling with dry-ice
  9. customto give 0.46 g

Sources & evidence

ORD record
ord-e7a0380d140f49b4981690e243d24d66
Source dataset
uspto-grants-1979_03
Patent number
US04146726

Reaction notes

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