Formaldehyde → HCID 54383407, compound

HRID 426940Notes

Reaction equation

HRID 426940 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[CH:8][C:9]([NH2:11])=[O:10])[C:4]([N+:12]([O-:14])=[O:13])=[N:3]1.[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[CH2:20]=O>CO>[N:15]1([CH2:20][NH:11][C:9](=[O:10])[CH:8]=[CH:7][C:5]2[C:4]([N+:12]([O-:14])=[O:13])=[N:3][N:2]([CH3:1])[CH:6]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 712Formaldehyde3×HCID 31268Pyrrolidine3×HCID 54282095HCID 54282095, compound

Product 1

HCID 54383407HCID 54383407, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 g. 3-(1-methyl-3-nitro-4-pyrazolyl)-acrylamide (preparation see Example 3) is mixed with 3.5 ml. methanol, 1 ml. pyrrolidine and 0.9 ml. 37% aqueous formaldehyde solution and stirred under reflux for 4 hours. A further 1 ml. pyrrolidine and 0.9 ml. formaldehyde solution are added thereto and the reaction mixture is kept under reflux for a further 3 hours. 1 ml. pyrrolidine and 0.9 ml. formaldehyde are again added thereto and stirring under reflux continued for a further 6 hours. The reaction mixture is then completely evaporated to dryness in a vacuum, the residue is triturated with methanol and the solid material is filtered off with suction. There is thus obtained 0.34 g. 3-(1-methyl-3-nitro-4-pyrazolyl)-acrylic acid N-(pyrrolidinomethyl)-amide; m.p. 180°-183° C. It is soluble in dilute hydrochloric acid. A further 0.35 g. of the same compound is obtained from the mother liquor by evaporation.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureunder reflux for a further 3 hours
  3. temperatureunder reflux
  4. customThe reaction mixture is then completely evaporated to dryness in a vacuum
  5. customthe residue is triturated with methanol
  6. filtrationthe solid material is filtered off with suction
  7. customof the same compound is obtained from the mother liquor by evaporation

Sources & evidence

ORD record
ord-e1dd065ff20d42349f42769bebb122e2
Source dataset
uspto-grants-1979_10
Patent number
US04172136

Reaction notes

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