N-bromobutanimide → HCID 14155309, compound

HRID 619943Notes

Reaction equation

HRID 619943 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.[Br:23]N1C(=O)CCC1=O>C(O)(=O)C.C(OC(=O)C)(=O)C>[Br:23][C:7]1[C:2]([CH3:1])=[N:3][C:4]2[N:5]([N:8]=[C:9]([S:11]([NH:14][C:15]3[C:16]([Cl:22])=[CH:17][CH:18]=[CH:19][C:20]=3[Cl:21])(=[O:13])=[O:12])[N:10]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14155248HCID 14155248, compound

Product 1

HCID 14155309HCID 14155309, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 4.0 g (11 mmol) of 5-methyl-N-(2,6-dichlorophenyl)-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamide in 50 ml of glacial acetic acid and 10 ml of acetic anhydride was stirred at 90° C. for 30 minutes. N-Bromosuccinimide (2.4 g, 13 mmol) was added to this hot solution, and the reaction mixture was stirred at 90° l C. for 60 minutes. The solution was cooled and poured into 200 ml of ice water. A solid which separated was collected and dried. This crude product was purified by dissolving the sample in methylene chloride, filtering the solution through silica gel and triturating the filtrate with pentane. The desired product was obtained as a solid, mp 215°-216° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

  1. stirringthe reaction mixture was stirred at 90° l C
  2. waitfor 60 minutes
  3. temperatureThe solution was cooled
  4. customA solid which separated
  5. customwas collected
  6. customdried
  7. customThis crude product was purified
  8. dissolutionby dissolving the sample in methylene chloride
  9. filtrationfiltering the solution through silica gel
  10. customtriturating the filtrate with pentane

Sources & evidence

ORD record
ord-75712e90ff4444d99f7c9026bbd53458
Source dataset
uspto-grants-1989_04
Patent number
US04818273

Reaction notes

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