Acetic Acid → 4-[1-Methoxycarbonyl-3-(5-nitro-2-furyl)pyrazol-4-ylmethyleneamino]morpholine

HRID 839214Notes

Reaction equation

HRID 839214 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH:9]=[C:8]([CH:10]=O)[C:7]([C:12]2[O:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[N:6]1)=[O:4].[NH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(O)(=O)C>CO>[CH3:1][O:2][C:3]([N:5]1[CH:9]=[C:8]([CH:10]=[N:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:7]([C:12]2[O:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)=[N:6]1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 20315N-AminomorpholineHCID 203259421-Methoxycarbonyl-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehyde

Product 1

HCID 706198014-[1-Methoxycarbonyl-3-(5-nitro-2-furyl)pyrazol-4-ylmethyleneamino]morpholineYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir together 6.7 g of 1-methoxycarbonyl-3-(5-nitro-2-furyl)pyrazole-4-carboxaldehyde, 2.85 g of 4-aminomorpholine and 1.6 ml of glacial acetic acid in 125 ml of methanol for 3 hours at room temperature. Cool the resulting admixture on ice to produce a precipitate. Vacuum filter the precipitate and then suspend it once more in ethanol to obtain a 70% yield of 4-[1-methoxycarbonyl-3-(5-nitro-2-furyl)pyrazol-4-ylmethyleneamino]morpholine [m.p. 184° C (with decomposition)].

Workup

  1. temperatureCool the resulting admixture on ice
  2. customto produce a precipitate
  3. filtrationVacuum filter the precipitate

Sources & evidence

ORD record
ord-c2fadde68f684bb28d53fd13f39c1486
Source dataset
uspto-grants-1978_06
Patent number
US04093812

Reaction notes

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