Tetrahydrofuran → 5-Amino-3-(4-chloro-1-naphthyl)-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazole

HRID 1289772Notes

Reaction equation

HRID 1289772 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([Cl:17])=[CH:9][CH:8]=2)[NH:4][N:3]=1.[OH-].[Na+].[CH3:20][N:21]=[C:22]=[S:23].O1CCCC1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:3]([C:22]([NH:21][CH3:20])=[S:23])[N:4]=[C:5]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([Cl:17])=[CH:9][CH:8]=2)[N:6]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11167Methyl isothiocyanateHCID 14798Sodium HydroxideHCID 107528543-Amino-5-(4-chloro-1-naphthyl)-1H-1,2,4-triazol

Product 1

HCID 105916075-Amino-3-(4-chloro-1-naphthyl)-1-[methylamino(thiocarbonyl)]-1H-1,2,4-triazoleYield 5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The synthesis method of Example 7-(3) was applied. The compound (2.19 g) obtained in (4) above, a 1N sodium hydroxide solution (10.0 ml), methyl isothiocyanate (1.38 g) and tetrahydrofuran (10 ml) were used as reagents. After the reaction, silica gel column chromatography (chloroform) and recrystallization from chloroform gave 135 mg of white crystals (yield 5% from methyl 4-chloro-1-naphthoate).

Sources & evidence

ORD record
ord-2974aa6beeca4219865fcf73d63b5b3e
Source dataset
uspto-grants-1998_05
Patent number
US05750545

Reaction notes

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