Bromobenzene → HCID 57619617, compound

HRID 545285Notes

Reaction equation

HRID 545285 reaction equation
[Cl:1][C:2]1[C:3]([OH:16])=[C:4]([C:11]([O:13]CC)=O)[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[CH3:8].[NH2:17][C:18]1[NH:19][C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=1.BrC1C=CC=CC=1>CCCCCC>[N:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[NH:22][C:18]=1[NH:17][C:11]([C:4]1[C:5](=[O:10])[N:6]([CH3:9])[C:7]([CH3:8])=[C:2]([Cl:1])[C:3]=1[OH:16])=[O:13]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 136242-AminobenzimidazoleHCID 57619613HCID 57619613, compound

Product 1

HCID 57619617HCID 57619617, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

199 mg of ethyl 5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate and 98 mg of 2-amino-benzimidazole were added to 2 ml of bromobenzene, then, the mixture was stirred for 9.5 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 202 mg of N-(2-benzimidazolyl)-5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide (hereinafter, referred to as present compound 28) 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-4820a7a14c6943cf8aadd7be7a9d0fb3
Source dataset
uspto-grants-2011_05
Patent number
US07935716B2

Reaction notes

Loading…