Pyridine → methyl N-[methyl(phenylsulfinothioyl)carbamoyl]oxyethanimidothioate

HRID 1154757Notes

Reaction equation

HRID 1154757 reaction equation
[CH3:1][NH:2][C:3]([O:5][N:6]=[C:7]([S:9][CH3:10])[CH3:8])=[O:4].N1C=CC=CC=1.[S:17](Cl)(Cl)=O.[C:21]1([SH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCCC1>[CH3:1][N:2]([S:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[S:17])[C:3]([O:5][N:6]=[C:7]([S:9][CH3:10])[CH3:8])=[O:4]

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 4109MethomylHCID 7969ThiophenolHCID 24386Thionyl Chloride

Product 1

HCID 131712178methyl N-[methyl(phenylsulfinothioyl)carbamoyl]oxyethanimidothioate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.3 g S-methyl N-[N'-methylcarbamoyloxy]thioacetimidate (0.02 mol), 1.9 g pyridine (0.024 mol) and 2.5 g thionyl chloride (0.021 mol), in 20 ml dry tetrahydrofuran was stirred at room temperature for 4 hours. Pyridine (1.9 g, 0.024 mol) was added and followed by 2.2 g benzenethiol (0.02 mol) added dropwise at water bath temperature. Stirring was continued for an additional hour, and the mixture was worked up as described for Example I. The resulting oily residue was purified by preparative thin-layer chromatography, and the NMR spectrum obtained.

Workup

  1. additionadded dropwise at water bath temperature
  2. waitwas continued for an additional hour
  3. customThe resulting oily residue was purified by preparative thin-layer chromatography
  4. customthe NMR spectrum obtained

Sources & evidence

ORD record
ord-00e4e54555514467b7762893811c0136
Source dataset
uspto-grants-1981_11
Patent number
US04298527

Reaction notes

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