Triethylamine → N-(3-cyanophenyl)-6-methyl-2,3-dihydro-1,4-oxathiine-5-carboxamide

HRID 1938844

Reaktionsgleichung

Reaktionsgleichung von HRID 1938844
[CH3:1][C:2]1[O:3][CH2:4][CH2:5][S:6][C:7]=1[C:8]([OH:10])=O.S(Cl)(Cl)=O.[NH2:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20].C(N(CC)CC)C>C(Cl)Cl>[C:19]([C:18]1[CH:17]=[C:16]([NH:15][C:8]([C:7]2[S:6][CH2:5][CH2:4][O:3][C:2]=2[CH3:1])=[O:10])[CH:23]=[CH:22][CH:21]=1)#[N:20]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 167023-AminobenzonitrileHCID 24386Thionyl ChlorideHCID 5399462-Methyl-5,6-dihydro-1,4-oxathiine-3-carboxylic acid

Produkt 1

HCID 507308N-(3-cyanophenyl)-6-methyl-2,3-dihydro-1,4-oxathiine-5-carboxamideAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

5,6-Dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid (5.0 g, 0.031 mole) and thionyl chloride (4.1 g, 0.034 mole) were heated under reflux in methylene chloride for about 2 hours, then evaporated under reduced pressure. The solid residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride and the chilled solution treated dropwise with a solution of 3-aminobenzonitrile (3.7 g, 0.031 mole) and triethylamine (3.2 g, 0.032 mole) in methylene chloride. The reaction mixture was stirred at room temperature for a further 3 hours and then worked up by washing with dilute hydrochloric acid and dilute sodium hydroxide. Evaporation of the solvent gave a solid residue, which was recrystallized from methanol to give a white solid, m.p. 119°-121° C. (5.5 g, 67% yield).

Aufarbeitung

  1. customevaporated under reduced pressure
  2. dissolutionThe solid residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride
  3. washby washing with dilute hydrochloric acid and dilute sodium hydroxide
  4. customEvaporation of the solvent
  5. customgave a solid residue, which
  6. customwas recrystallized from methanol
  7. customto give a white solid, m.p. 119°-121° C. (5.5 g, 67% yield)

Quellen und Nachweise

ORD-Eintrag
ord-5ba29017ec7940868d6c8e1212387385
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05693827

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