N-Methylhydrazinecarbothioamide → 5-ethyl-4-methyl-4H-1,2,4-triazole-3-thiol

HRID 602584Notes

Reaction equation

HRID 602584 reaction equation
[CH3:1]N1C=NNC1=O.I[CH2:9][C:10]1[N:14]([CH3:15])[C:13]([S:16](C)(=O)=O)=[N:12][N:11]=1.CNC(=S)NN>>[CH2:9]([C:10]1[N:14]([CH3:15])[C:13](=[S:16])[NH:12][N:11]=1)[CH3:1]

Participants

4

Reactant 3

HCID 2723853N-MethylhydrazinecarbothioamideHCID 111476744114-43-6HCID 59820596HCID 59820596, compound

Product 1

HCID 38297955-ethyl-4-methyl-4H-1,2,4-triazole-3-thiol

Procedure

Introduction of the 4-methyl-2,4-dihydro-[1,2,4]triazol-3-one moiety is accomplished by O-alkylation of A-5 with 3-iodomethyl-5-methanesulfonyl-4-methyl-4H-[1,2,4]triazole which is prepared as depicted in SCHEME B. Condensation of ethyl hydroxy acetate and 4-methyl-3-thiosemicarbazide afforded 5-ethyl-4-methyl-2,4-dihydro-[1,2,4]triazole-3-thione (B-3) which is S-alkylated (step 2), converted to the chloromethyl compound (step 3), oxidized to the sulfone (step 4) and converted to the desired iodomethyl compound B-5b via a Finkelstein reaction (step 5).

Workup

  1. customis prepared

Sources & evidence

ORD record
ord-d360c52067754098b145050412a2a840
Source dataset
uspto-grants-2011_03
Patent number
US07906540B2

Reaction notes

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