Triethylamine → S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)-carbamoyloxy]thioacetimidate

HRID 1447116Notes

Reaction equation

HRID 1447116 reaction equation
[CH3:1][SH-:2][C:3](=[N:5][OH:6])[CH3:4].[CH3:7][N:8]([S:12][N:13]([CH3:15])[CH3:14])[C:9](F)=[O:10].C(N(CC)CC)C>O1CCCC1>[CH3:7][N:8]([S:12][N:13]([CH3:15])[CH3:14])[C:9]([O:6][N:5]=[C:3]([S:2][CH3:1])[CH3:4])=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12799216N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluorideHCID 178504139HCID 178504139, compound

Product 1

HCID 54514859S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)-carbamoyloxy]thioacetimidateYield 13.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5.25 g (0.05 mole) of S-methyl-N-hydroxythioacetimidate, 7.9 g of N-methyl-N-(dimethylaminosulfenyl)carbamoyl fluoride, and 5.1 g of triethylamine in 75 ml of tetrahydrofuran was stirred and heated at 40°-60° C. for 3 hrs. and then at 25° C. for 8 hrs. The solvent was removed in vacuo, and the residue was taken up in chloroform. This solution was extracted with water and 10% potassium carbonate, dried (MgSO4) and then was concentrated in vacuo. The crude syrupy residue obtained was purified by column chromatography on silica gel to give 1.6 g of S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)-carbamoyloxy]thioacetimidate, a yellow syrup.

Workup

  1. temperatureheated at 40°-60° C. for 3 hrs
  2. customThe solvent was removed in vacuo
  3. extractionThis solution was extracted with water and 10% potassium carbonate
  4. dry with materialdried (MgSO4)
  5. concentrationwas concentrated in vacuo
  6. customThe crude syrupy residue obtained
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4c6df717029f49239356f3196aae47c9
Source dataset
uspto-grants-1982_02
Patent number
US04315928

Reaction notes

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