Hydrochloric Acid → 5-n-Butyl-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36250

Reaction equation

HRID 36250 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[NH:11][NH2:12].Cl.Cl[C:15]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=C[C:16]=1N.C1C[O:28][CH2:27]C1>>[CH2:20]([C:19]1[NH:22][C:27](=[O:28])[N:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[Cl:1])[N:12]=1)[CH2:21][CH2:15][CH3:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 226912-Chloro-5-nitroanilineHCID 4103137(2-Chloro-5-nitrophenyl)hydrazine

Product 1

HCID 1354641015-n-Butyl-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 19%

Procedure

By the procedure of Example 4, Step C, 2-chloro-5-nitrophenylhydrazine [generated from the hydrochloride, which was prepared from 2-chloro-5-nitroaniline according to H. Stroh and G. Westphal, Chem. Ber. 96, 184 (1963), by partitioning between ether and 1N sodium carbonate] was reacted with ethyl N-carbethoxyvalerimidate (from Example 4, Step B). Enough THF was added to the reaction mixture to ensure dissolution of all starting material. After work-up, the residue was purified by flash chromatography on silica gel (gradient elution with 0.5-5.0% methanol in CH2Cl2) to give a 19% yield of the title compound as an orange solid, mp 145°-147° C., homogeneous by TLC (19:1 CH2Cl2 --MeOH), mass spectrum (FAB) m/e 297 (M+1)+.

Workup

  1. custom96, 184 (1963), by partitioning between ether and 1N sodium carbonate]
  2. customwas reacted with ethyl N-carbethoxyvalerimidate (from Example 4, Step B)
  3. dissolutiondissolution of all starting material
  4. customAfter work-up, the residue was purified by flash chromatography on silica gel (gradient elution with 0.5-5.0% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-74462da14cec4b19b8156301e23fb146
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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