Methyl iodide → S,N-dimethyl-N'-nitroisothiourea

HRID 1711169Notes

Reaction equation

HRID 1711169 reaction equation
[CH3:1][S:2][C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].[C:9]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C.O.CCOC(C)=O>[N+:5]([NH:4][C:3]([S:2][CH3:1])=[N:8][CH3:9])([O-:7])=[O:6]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 11051832S,N-dimethyl-N'-nitroisothioureaYield 11.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methyl-1-nitro-2-thiopseudourea (430 mg, 3.19 mmol) in DMF (3 ml) was added Cs2CO3 (1.10 g, 3.38 mmol) and MeI (0.30 ml, 4.82 mmol) and the reaction stirred overnight. The mixture was then diluted with water (10 ml) and EtOAc (40 ml) and the organic layer washed with brine (3×15 ml), dried (Na2SO4) and concentrated. The resultant yellow oil was purified by column chromatography on silica gel (EtOAc/Hexanes, 1:1) to afford S-methyl N-nitro-N′-methylcarbamimidothioate (56 mg, 11%) as a white solid. 1H NMR (CDCl3) δ 2.52 (s, 3H), 3.12 (d, 3H, J=6 Hz), 10.05 (br s, 1H).

Workup

  1. washthe organic layer washed with brine (3×15 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe resultant yellow oil was purified by column chromatography on silica gel (EtOAc/Hexanes, 1:1)

Sources & evidence

ORD record
ord-040186826e2242a6864a3965debb5c31
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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