Triethylamine → N,N-diethyl-3-(N',N'-diethylthiocarbamoyloxy)picolinamide

HRID 52130

Reaktionsgleichung

Reaktionsgleichung von HRID 52130
[OH:1][C:2]1[C:3]([C:8]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.CN1C(=O)N(C)CCC1.C(N(CC)CC)C.[CH2:31]([N:33]([CH2:37][CH3:38])[C:34](Cl)=[S:35])[CH3:32]>O>[CH2:11]([N:10]([CH2:13][CH3:14])[C:8](=[O:9])[C:3]1[C:2]([O:1][C:34](=[S:35])[N:33]([CH2:37][CH3:38])[CH2:31][CH3:32])=[CH:7][CH:6]=[CH:5][N:4]=1)[CH3:12]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 66607Diethylthiocarbamoyl chlorideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 3020810N,N-diethyl-3-hydroxypyridine-2-carboxamide

Produkt 1

HCID 19963243N,N-diethyl-3-(N',N'-diethylthiocarbamoyloxy)picolinamideAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

258.3 g (1.33 mol) of 3-hydroxy-N,N-diethylpicolinamide are introduced into 1 l of dimethylpropyleneurea and 213.2 ml (1.53 mol) of triethylamine at 0° C., and 222 g (1.464 mol) of diethylthiocarbamoyl chloride are introduced in the form of a solid. After the reaction mixture has been stirred for 2 hours at 0° C., it is poured into 2 l of water and extracted three times using ethyl acetate, the ethyl acetate phases are washed five times using 500 ml of water in each case, and the combined organic phases are dried over Na2SO4 and concentrated in vacuo at 60° C. Recrystallization from Et2O/hexane gives 341 g (83%) of brown crystals, m.p. 70°-72° C.

Aufarbeitung

  1. extractionextracted three times
  2. washthe ethyl acetate phases are washed five times
  3. dry with materialthe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated in vacuo at 60° C
  5. customRecrystallization from Et2O/hexane

Quellen und Nachweise

ORD-Eintrag
ord-7f4daed40d314eedb8125aa00e940a83
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616590

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