N-bromobutanimide → HCID 59295129, compound

HRID 1045725Notes

Reaction equation

HRID 1045725 reaction equation
[Cl:1][C:2]1[C:3]([NH:8][NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[N:4][CH:5]=[CH:6][N:7]=1.[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[Br:16][C:6]1[N:7]=[C:2]([Cl:1])[C:3]([NH:8][NH:9][C:10](=[O:15])[C:11]([F:12])([F:13])[F:14])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58446973HCID 58446973, compound

Product 1

HCID 59295129HCID 59295129, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 500 mL round bottom flask was charged with N′-(3-chloropyrazin-2-yl)-2,2,2-trifluoroacetohydrazide (7.76 g, 32.3 mmol) and CHCl3 (200 mL). To the above solution was added N-bromosuccinimide (8.63 g, 48.5 mmol) at 0° C. The resulting mixture was stirred at room temperature for 1 h. Reaction progress was monitored by TLC (EtOAc/petroleum ether=1:2). Work-up: the reaction mixture was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 20% EtOAc in petroleum ether, to afford 2.97 g (29%) of the product as a light yellow solid.

Workup

  1. customReaction progress
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel with 20% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-6167abcce76c45ce864d2e139081bc41
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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