Bromobenzene → HCID 178427958, compound

HRID 1873746Notes

Reaction equation

HRID 1873746 reaction equation
[Cl:1][C:2]1[C:3]([OH:16])=[C:4]([C:11](OCC)=[O:12])[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[CH3:8].[NH2:17][C:18]1[N:22]=[CH:21][NH:20][N:19]=1.BrC1C=CC=CC=1>CCCCCC>[Cl:1][C:2]1[C:3]([OH:16])=[C:4]([C:11]([NH:17][C:18]2[N:22]=[CH:21][NH:20][N:19]=2)=[O:12])[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 57619613HCID 57619613, compoundHCID 178418311HCID 178418311, compound

Product 1

HCID 178427958HCID 178427958, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

161 mg of ethyl 5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate and 51 mg of 3-amino-1,2,4-triazole were added to 1.5 ml of bromobenzene, then, the mixture was stirred for 5 hours under heat refluxing condition. The reaction mixture was cooled to room temperature, then, hexane was added to this and the resultant mixture was allowed to stand still. The resulting solid was collected by filtration, and washed with a mixture of t-butyl methyl ether and n-hexane and dried to obtain 153 mg of 5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-N-(1,2,4-triazol-3-yl)-1,2-dihydropyridine-3-carboxamide (hereinafter, referred to as present compound 29) represented by the formula:

Workup

  1. temperatureunder heat
  2. temperaturerefluxing condition
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with a mixture of t-butyl methyl ether and n-hexane
  5. customdried

Sources & evidence

ORD record
ord-94bf12cb00fb4891a68ebf76b7d0611d
Source dataset
uspto-grants-2012_11
Patent number
US08304437B2

Reaction notes

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