2-Aminothiazole → HCID 57619640, compound

HRID 1873747Notes

Reaction equation

HRID 1873747 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[S:19][CH:20]=[CH:21][N:22]=1.BrC1C=CC=CC=1>CCCCCC>[Cl:1][C:2]1[C:3]([OH:16])=[C:4]([C:11]([NH:17][C:18]2[S:19][CH:20]=[CH:21][N:22]=2)=[O:13])[C:5](=[O:10])[N:6]([CH3:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 7961BromobenzeneHCID 57619613HCID 57619613, compound

Product 1

HCID 57619640HCID 57619640, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

160 mg of ethyl 5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-1,2-dihydropyridine-3-carboxylate and 60 mg of 2-aminothiazole 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 136 mg of 5-chloro-1,6-dimethyl-4-hydroxy-2-oxo-N-(2-thiazolyl)-1,2-dihydropyridine-3-carboxamide (hereinafter, referred to as present compound 30) 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-1e8cb8135283402bae2971f746c5ffdd
Source dataset
uspto-grants-2012_11
Patent number
US08304437B2

Reaction notes

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