Methylamine → Methyl N-(methanesulfonyl)-N'-methylcarbamimidothioate

HRID 1711168Notes

Reaction equation

HRID 1711168 reaction equation
[CH3:1][S:2][C:3](SC)=[N:4][S:5]([CH3:8])(=[O:7])=[O:6].[CH3:11][NH2:12].C1COCC1>CO>[CH3:8][S:5]([NH:4][C:3]([S:2][CH3:1])=[N:12][CH3:11])(=[O:7])=[O:6]

Participants

5

Reactant 3

HCID 6329Methylamine2×HCID 8028TetrahydrofuranHCID 13449843N-[bis(methylsulfanyl)methylidene]methanesulfonamide

Product 1

HCID 13247984Methyl N-(methanesulfonyl)-N'-methylcarbamimidothioateYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-methanesulfonylcarbonimidodithioic acid dimethyl ester (1.5 g, 8.02 mmol) in MeOH (15 ml) was added a solution of methylamine in THF (2.0 M, 4.8 ml, 9.6 mmol) and the reaction heated to 50° C. for 2.5 h before another portion of methylamine was added (4.8 ml, 9.6 mmol) and the reaction heated to 50° C. for an additional 1 h. The mixture was concentrated and purified by column chromatography on silica gel (EtOAc/Hexanes, 1:1) to afford S-methyl N-methanesulfonyl-N′-methylcarbamimidothioate (0.95 g, 70%) as a clear oil. 1H NMR (CDCl3) δ 2.40 (s, 3H), 2.96 (d, 3H, J=6 Hz), 3.01 (s, 3H), 7.95 (br s, 1H).

Workup

  1. additionwas added (4.8 ml, 9.6 mmol)
  2. concentrationThe mixture was concentrated
  3. custompurified by column chromatography on silica gel (EtOAc/Hexanes, 1:1)

Sources & evidence

ORD record
ord-d7376d7c175b4f4885b92aef4e4cdf3d
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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