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

HRID 1447116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1447116
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 54514859S-methyl N-[N'-methyl-N'-(dimethylaminosulfenyl)-carbamoyloxy]thioacetimidateAusbeute 13,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4c6df717029f49239356f3196aae47c9
Quelldatensatz
uspto-grants-1982_02
Patentnummer
US04315928

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