Benzoyl chloride → HCID 14155371, compound

HRID 619945Notes

Reaction equation

HRID 619945 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([S:11]([NH:14][C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])(=[O:13])=[O:12])[N:10]=[C:4]2[N:3]=1.C([O-])([O-])=O.[K+].[K+].[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([S:11]([N:14]([C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:15]3[C:16]([Cl:22])=[CH:17][CH:18]=[CH:19][C:20]=3[Cl:21])(=[O:13])=[O:12])[N:10]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 14155248HCID 14155248, compound

Product 1

HCID 14155371HCID 14155371, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 3.00 g (8.37 mmol) of 5-methyl -N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide and 1.16 g (8.37 mmol) of anhydrous powdered K2CO3 in 100 ml of acetone was heated at reflux for 30 minutes. A solution of 1.18 g (8.37 mmol) of benzoyl chloride in 10 ml of acetone was added, and the reaction was heated at reflux for 115 min. The reaction was filtered, and the filtrate was evaporated at reduced pressure. The solid residue was collected by filtration, washed thoroughly with aqueous NaHCO3 and H2O and dried to yield 2.7, g (72%) of the desired product as a solid, mp 187°-189° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 115 min
  5. filtrationThe reaction was filtered
  6. customthe filtrate was evaporated at reduced pressure
  7. filtrationThe solid residue was collected by filtration
  8. washwashed thoroughly with aqueous NaHCO3 and H2O
  9. customdried
  10. customto yield 2.7

Sources & evidence

ORD record
ord-8e883acbe3094435a6ecc6ed980e335c
Source dataset
uspto-grants-1989_04
Patent number
US04818273

Reaction notes

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