Bromobenzene → HCID 57619628, compound

HRID 545273Notes

Reaction equation

HRID 545273 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[S:19][CH:20]=[N:21][N:22]=1.BrC1C=CC=CC=1>CCCCCC>[S:19]1[CH:20]=[N:21][N: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:12]

Participants

5

Reactant 3

HCID 7961BromobenzeneHCID 199091,3,4-Thiadiazol-2-amineHCID 57619613HCID 57619613, compound

Product 1

HCID 57619628HCID 57619628, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

197 mg of ethyl 5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate and 76 mg of 2-amino-1,3,4-thiadiazole were added to 2 ml of bromobenzene, then, the mixture was stirred for 5 hours under heat refluxing condition. The reaction mixture was cooled to room temperature, then, to the reaction mixture was added n-hexane. The resulting solid was collected by filtration, and washed with a mixture of t-butyl methyl ether and n-hexane and dried to obtain 183 mg of N-(1,3,4-thiadiazol-2-yl)-5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxamide (hereinafter, referred to as present compound 14) 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-16c806c23d324dc99689ab0281dd14da
Source dataset
uspto-grants-2011_05
Patent number
US07935716B2

Reaction notes

Loading…