Butyl isocyanate → N-(Butylcarbamoyl)-2-methyl-5-nitropyridine-3-carboxamide

HRID 972758Notes

Reaction equation

HRID 972758 reaction equation
[CH3:1][C:2]1[N:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[CH2:14]([N:18]=[C:19]=[O:20])[CH2:15][CH2:16][CH3:17]>C1(C)C=CC=CC=1>[CH2:14]([NH:18][C:19](=[O:20])[NH:6][C:4]([C:3]1[C:2]([CH3:1])=[N:10][CH:9]=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=1)=[O:5])[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 8110Butyl isocyanateHCID 214052702-Methyl-5-nitropyridine-3-carboxamide

Product 1

HCID 53864046N-(Butylcarbamoyl)-2-methyl-5-nitropyridine-3-carboxamideYield 43.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.9 g of 2-methyl-5-nitronicotinamide and 0.9 g of n-butylisocyanate in 40 ml of anhydrous toluene was refluxed for 18 hours. Unreacted nicotinamide (0.2 g) was filtered off and the filtrate was chromatographed over silica gel to give 0.6 g of the desired product. mp 111° - 112° C.

Workup

  1. temperaturewas refluxed for 18 hours
  2. filtrationUnreacted nicotinamide (0.2 g) was filtered off
  3. customthe filtrate was chromatographed over silica gel

Sources & evidence

ORD record
ord-6298fcc7effe433b9f5a581fd10e12fe
Source dataset
uspto-grants-1977_10
Patent number
US04053608

Reaction notes

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