Methyl iodide → Methyl 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbimidothioate hydroiodide

HRID 570940

Reaction equation

HRID 570940 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[N:6]2[CH:9]=[N:10][C:11]([C:12](=[S:14])[NH2:13])=[C:5]2[N:4]=[N:3]1.[CH3:15][I:16]>C(#N)C>[IH:16].[CH3:1][N:2]1[C:7](=[O:8])[N:6]2[CH:9]=[N:10][C:11]([C:12]([S:14][CH3:15])=[NH:13])=[C:5]2[N:4]=[N:3]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 33528803-Methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide

Product 1

HCID 66831606Methyl 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbimidothioate hydroiodideYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-methyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carbothioamide (2.75 g, 13.1 mmol) and methyl iodide (8.2 mL, 131 mmol) in acetonitrile (900 mL) was stirred at room temperature for 3 days. The mixture was concentrated under vacuum and the solid was suspended in diethyl ether. The precipitate was filtered and washed with diethyl ether to give the pure title compound as an orange solid (4.03 g, 88% yield). δH (DMSO-d6): 11.6 (1H, bs), 9.18 (1H, s) 3.94 (3H, s), 2.82 (3H, s).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. filtrationThe precipitate was filtered
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-f5e14e63d54e413c89dae841aa3c9064
Source dataset
uspto-grants-2015_05
Patent number
US09024018B2

Linked notes

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