N-bromobutanimide → HCID 14155309, compound

HRID 844985Notes

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

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° 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 fitrate with pentane. The desired product was obtained as a solid, m.p. 215°-216° C. IR and 1H NMR spectra were in agreement with the assigned structure.

Workup

stirringthe reaction mixture was stirred at 90° C. for 60 minutes
temperatureThe solution was cooled
customA solid which separated
customwas collected
customdried
customThis crude product was purified
dissolutionby dissolving the sample in methylene chloride
filtrationfiltering the solution through silica gel
customtriturating the fitrate with pentane

Sources & evidence

ORD record: ord-20a40676ad18405192629409cc2e729b
Source dataset: uspto-grants-1988_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04755212

Reaction notes

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