Benzoyl chloride → HCID 19872301, compound

HRID 477730Notes

Reaction equation

HRID 477730 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][S:10]([C:13]1[N:17]=[C:16]([CH3:18])[N:15]([C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:14]=1)(=[O:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CC(C)=O>[C:31]([N:9]([C:3]1[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=1[F:8])[S:10]([C:13]1[N:17]=[C:16]([CH3:18])[N:15]([C:19]2[N:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[N:14]=1)(=[O:11])=[O:12])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 54332626HCID 54332626, compound

Product 1

HCID 19872301HCID 19872301, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A suspension of N-(2,6-difluorophenyl)-5-methyl-1-(2-pyrimidinyl)-1,2,4-triazole-3-sulphonamide (1.5 g) (Compound A54) and anhydrous potassium carbonate (0.59 g) in dry acetone (50 ml) was heated under reflux for 30 minutes. A solution of benzoyl chloride (0.6 g) in acetone (50 ml) was added, and the mixture was refluxed for a further 2 hours. The mixture was then allowed to stand at 25° C. for 18 hours, after which it was warmed, filtered and evaporated. The solid produced was recrystallised from acetonitrile to give 1.05 g of the desired product, mp 218°-221° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturethe mixture was refluxed for a further 2 hours
  4. temperatureafter which it was warmed
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid produced
  8. customwas recrystallised from acetonitrile

Sources & evidence

ORD record
ord-08c8d8a1765e4eff80430357a56f25bd
Source dataset
uspto-grants-1989_12
Patent number
US04889553

Reaction notes

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