1,2-Dibromopropane → 5,6-Dihydro-6-methyl-3-(2-thienyl)-1,4,2-oxadiazine

HRID 1955951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1955951
CS[C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=S.Cl.[NH2:11][OH:12].C([N:15]([CH2:18][CH3:19])CC)C.Br[CH2:21]C(Br)C>CO.O>[CH3:21][CH:19]1[O:12][NH:11][C:3]([C:5]2[S:6][CH:7]=[CH:8][CH:9]=2)=[N:15][CH2:18]1

Komponenten

7

Edukt 4

HCID 65531,2-DibromopropaneHCID 8471Triethylamine3×HCID 443297Hydroxyamine hydrochloride2×HCID 12473607Methyl thiophene-2-carbodithioate

Produkt 1

HCID 226173535,6-Dihydro-6-methyl-3-(2-thienyl)-1,4,2-oxadiazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

Methyl-2-thiophenecarbodithioate (47 g, 0.27 mol) in methanol (250 ml) at 0°-5° C., was stirred and treated with powdered hydroxylamine hydrochloride (20 g) and followed by dropwise addition of triethylamine (50 ml) in methanol (50 ml) over 2 hours, to prepare a reaction mixture. Additional hydroxylamine hydrochloride (5 g) and triethylamine (10 ml) was added consecutively to the reaction mixture and after 45 minutes, the reaction mixture turned yellow (from red). 1,2-Dibromopropane (26 ml) was then added to the yellow reaction mixture, followed by addition of triethylamine (75 ml). The resultant new reaction mixture was refluxed for 4 hours and then left overnight at ambient temperature. The methanol was removed from the reaction mixture to leave a residue. Water was added to the residue which was then extracted into ethyl acetate, washed with dilute hydrochloric acid (2N, 100 ml), water, and dried (MgSO4). The ethyl acetate was then removed to leave a brown oil which was crystallized with cyclohexane to produce two crops of 5,6-dihydro-6-methyl-3-(2-thienyl)-1,4,2-oxadiazine (11.7 g and 3.7 g, mp 70°-72° C.) Found: C 48.90, H 4.66, N 7.17, C8H9 NOS2 requires C 48.24, H 4.52, N 7.07.

Aufarbeitung

  1. customto prepare a reaction mixture
  2. temperatureThe resultant new reaction mixture was refluxed for 4 hours
  3. customThe methanol was removed from the reaction mixture
  4. customto leave a residue
  5. extractionwas then extracted into ethyl acetate
  6. washwashed with dilute hydrochloric acid (2N, 100 ml), water
  7. dry with materialdried (MgSO4)
  8. customThe ethyl acetate was then removed
  9. customto leave a brown oil which
  10. customwas crystallized with cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-efee90312baf46d5991080abe39afd94
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05777110

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