Benzene → HCID 13020351, compound

HRID 461594Notes

Reaction equation

HRID 461594 reaction equation
C1C=CC=CC=1.C(N(CC)CC)C.[CH3:14][N:15]1[C:19]([OH:20])=[C:18]([C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[C:17]([CH3:31])=[N:16]1.[Cl:32][CH2:33][C:34](Cl)=[O:35]>CCOCC>[CH3:14][N:15]1[C:19]([O:20][C:34](=[O:35])[CH2:33][Cl:32])=[C:18]([C:21](=[O:30])[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[C:17]([CH3:31])=[N:16]1

Participants

6

Reactant 4

HCID 241Benzene2×HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 178434070HCID 178434070, compound

Product 1

HCID 13020351HCID 13020351, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a mixture of 10 ml. of benzene and 0.2 ml. of triethylamine is dissolved 0.285 g. of 1,3-dimethyl-4-(2.4-dichlorobenzoyl)-5-hydroxypyrazole and then a solution of 0.18 g. of chloroacetylchloride in 5 ml. of benzene is added dropwise under ice-cooling and stirring. After completion of the dropwise addition, the resulting mixture is stirred at room temperature for 2 hours. After completion of the reaction, ether is added to the reaction mixture and the mixture is then washed successively with 3 portions of 50 ml. of water and dried over anhydrous sodium sulfate. Then, the solvent is distilled off from the mixture and the resulting residue is recrystallized from n-hexane to give 0.297 g. of the desired product as white crystals melting at 120°-122° C. Yield 82.0%.

Workup

  1. additionIn a mixture of 10 ml
  2. temperaturecooling
  3. additionAfter completion of the dropwise addition
  4. stirringthe resulting mixture is stirred at room temperature for 2 hours
  5. additionis added to the reaction mixture
  6. washthe mixture is then washed successively with 3 portions of 50 ml
  7. dry with materialof water and dried over anhydrous sodium sulfate
  8. distillationThen, the solvent is distilled off from the mixture
  9. customthe resulting residue is recrystallized from n-hexane
  10. customto give 0.297 g

Sources & evidence

ORD record
ord-c9460b9b94654257a4fbd4249f0cf8b4
Source dataset
uspto-grants-1977_12
Patent number
US04063925

Reaction notes

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