Dichloromethane → 5-n-Butyl-2-[2-chloro-5-(methoxycarbonyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 36283

Reaction equation

HRID 36283 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH:12][NH2:13].[C:14]([N:19]=[C:20](OCC)[CH2:21][CH2:22][CH2:23][CH3:24])(OCC)=[O:15].C(Cl)Cl>CO>[CH2:21]([C:20]1[NH:19][C:14](=[O:15])[N:12]([C:3]2[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=2[Cl:1])[N:13]=1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 292358Methyl 4-chloro-3-hydrazinylbenzoateHCID 53930077ethyl N-carbethoxyvalerimidate

Product 1

HCID 1357200825-n-Butyl-2-[2-chloro-5-(methoxycarbonyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-oneYield 37%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

By the procedure of Example 4, Step C, the title compound was prepared from methyl 4-chloro-3-hydrazinobenzoate (from Step B) and ethyl N-carbethoxyvalerimidate (from Example 4, Step B) in 37% yield as an orange gum (TLC in 95:5 CH2Cl2 --MeOH), mass spectrum (FAB) m/e 310 (M+1)+.

Sources & evidence

ORD record
ord-f823704f88f141b384feb5badfe9a1a0
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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