5-Nitro-2-Furoic Acid → N-(3-Methyl-2-butenyl)-5-nitro-2-furancarboxamide

HRID 1779753Notes

Reaction equation

HRID 1779753 reaction equation
[N+:1]([C:4]1[O:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:25][C:26]([CH3:30])=[CH:27][CH2:28][NH2:29].C([O-])(O)=O.[Na+]>CN(C=O)C.CO.ClCCl>[CH3:25][C:26]([CH3:30])=[CH:27][CH2:28][NH:29][C:9]([C:7]1[O:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:11]

Participants

7

Reactant 4

HCID 125775-Nitro-2-Furoic Acid2×HCID 682631,1'-Carbonyldiimidazole2×HCID 516892Sodium BicarbonateHCID 183265643-Methylbut-2-en-1-amine hydrochloride

Product 1

HCID 18929144N-(3-Methyl-2-butenyl)-5-nitro-2-furancarboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21226129Dichloromethane methanolSolvent

Procedure

5-Nitro-2-furoic acid (5 q, 0.032 mol) was dissolved in dry DMF (25 mL). To this solution was added 1,1'-carbonyldiimidazole (5.7 g, 0.035 mol). The mixture was stirred at room temperature for 15 min; an orange colored suspension was formed. 3-Methyl-2-butenyl amine hydrochloride (3.9 g, 0.032 mol) was suspended in dry DMF (15 mL) in an Erlenmeyer flask and neutralized with NaHCO3, and the amine suspension was slowly added to the 5-nitro-2-furanoic acid and 1,1'-carbonyldiimidazole reaction mixture. The reaction mixture was stirred at room temperature for 2 h. TLC (silica gel, 10% methanol-dichloromethane, Rf =0.45) indicated completion. DMF was removed on a rotary evaporator and the residue was stirred with water (800 mL) to give a yellow solid. Yield: 3.3 g (46%). mp 92°-94° C. MS m/z, 448 (2M)+, 242 (M+NH4)+, 225 (M+H)+. 1H NMR (DMSO-d6) ε 1.73 [d, 6H, (CH3)2C=], 3.86 (t, 2H, CH2CH=), 5.22 (t, 1H, CH2CH=), 7.40 and 7.78 (d, 2H, furanyl-H), 8.96 (t, 1H, NHCO).

Workup

  1. customan orange colored suspension was formed
  2. stirringThe reaction mixture was stirred at room temperature for 2 h
  3. customDMF was removed on a rotary evaporator
  4. stirringthe residue was stirred with water (800 mL)
  5. customto give a yellow solid

Sources & evidence

ORD record
ord-19246b357de94cd493e11d4c50607bf6
Source dataset
uspto-grants-1997_05
Patent number
US05627286

Reaction notes

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