Benzene → HCID 13420349, compound

HRID 637598Notes

Reaction equation

HRID 637598 reaction equation
[Cl:1][C:2]1[C:16]([CH3:17])=[C:15]([Cl:18])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:12])[C:10]=1[OH:11])=[O:5].C1C=CC=CC=1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(N(CC)CC)C>[Cl:1][C:2]1[C:16]([CH3:17])=[C:15]([Cl:18])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:12])[C:10]=1[O:11][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:5]

Participants

5

Reactant 3

HCID 241BenzeneHCID 7498Benzyl BromideHCID 178427933HCID 178427933, compound

Product 1

HCID 13420349HCID 13420349, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1.43 g (0.005 mol) of 4-(2,4-dichloro-3-methylbenzoyl)-1-methyl-5-hydroxypyrazole was dissolved in 20 ml of benzene containing 0.50 g (0.005 mol) of triethylamine, and 0.86 g (0.005 mol) of benzylbromide was added thereto. Then, the reaction mixture was refluxed with stirring for 2 hours. After cooling, the precipitated salt was filtered off, and benzene was distilled off from the residual solution under reduced pressure. The resulting oily product was purified through a silica gel column chromatography (eluent:benzene) to obtain 1.67 g of the title compound (yield 89%).

Workup

  1. additionwas added
  2. temperatureThen, the reaction mixture was refluxed
  3. temperatureAfter cooling
  4. filtrationthe precipitated salt was filtered off
  5. distillationbenzene was distilled off from the residual solution under reduced pressure
  6. customThe resulting oily product was purified through a silica gel column chromatography (eluent:benzene)

Sources & evidence

ORD record
ord-2a31f677444047a7a29b4097cd08c857
Source dataset
uspto-grants-1985_12
Patent number
US04557753

Reaction notes

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