Bromobenzene → HCID 57619617, compound

HRID 1873745Notes

Reaction equation

HRID 1873745 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-cdfcb7042bd2464c83eaa55daa49944f
Source dataset
uspto-grants-2012_11
Patent number
US08304437B2

Reaction notes

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