Pyridine → 4-Nitro-N-(1,3-thiazol-2-yl)benzamide

HRID 2243433Notes

Reaction equation

HRID 2243433 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.N1C=CC=CC=1.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]>ClCCCl>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[O:21])=[CH:23][CH:24]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 21552-AminothiazoleHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 2303634-Nitro-N-(1,3-thiazol-2-yl)benzamideYield 96%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

2-Aminothiazole (100 mmol) was suspended in 1,2-dichloroethane (200 mL) and pyridine (100 mmol) was added. The mixture was added portion wise to a suspension of 4-nitro benzoic acid chloride (150 mmol) in 1,2-dichloroethane (500 mL) and stirred at 60° C. over night. The reaction mixture was cooled and filtered. The filtrate was washed with 1,2-dichloroethane and dried in vacuo to give 4-nitro-N-thiazol-2-yl-benzamide.

Workup

  1. additionThe mixture was added portion
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. washThe filtrate was washed with 1,2-dichloroethane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-897392f68707407c831bba52d0a22bb6
Source dataset
uspto-grants-2010_03
Patent number
US07674912B2

Reaction notes

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