Hexamethylenetetramine → 1-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbaldehyde

HRID 839199Notes

Reaction equation

HRID 839199 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[O:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=2)=[N:3]1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:27](O)=[O:28].C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:1][N:2]1[CH:6]=[C:5]([CH:27]=[O:28])[C:4]([C:7]2[O:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=2)=[N:3]1

Participants

5

Reactant 4

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 203260121-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole

Product 1

HCID 203259351-Methyl-3-(5-nitrofuran-2-yl)-1H-pyrazole-4-carbaldehydeYield 79%

Procedure

Heat 1.0 g of 1-methyl-3-(5-nitro-2-furyl)pyrazole together with 0.73 g of hexamethylenetetramine and 11.6 g of trifluoroacetic acid for 4.5 hours at boiling point. Add the resulting 4-pyrazolylmethyleneammonium-salt-containing solution to 31 ml of ice water. Stir the thus-obtained admixture for 15 minutes, and make it alkaline with concentrated sodium carbonate solution. Filter off the precipitate and wash it with water until it is neutral to obtain 1-methyl-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehyde [melting point: 181° to 182° C] with a yield of 79%.

Workup

  1. filtrationFilter off the precipitate
  2. washwash it with water until it

Sources & evidence

ORD record
ord-60e08213b9154f3688eb423d28fc3a16
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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