Triethylamine → 4-(3'-Methylanilino)-6-methylthiomethylquinazoline

HRID 52041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 52041
[CH3:1][S-:2].[Na+].Br[CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][N:10]=[C:9]2[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[NH:16][C:9]1[C:8]2[C:13](=[CH:14][CH:15]=[C:6]([CH2:5][S:2][CH3:1])[CH:7]=2)[N:12]=[CH:11][N:10]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 4378561Sodium methanethiolateHCID 224784026-Bromomethyl-4-(3-methylanilino)quinazoline

Produkt 1

HCID 199631224-(3'-Methylanilino)-6-methylthiomethylquinazolineAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium methanethiolate (0.141 g) was added to a stirred mixture of 6-bromomethyl-4-(3'-methylanilino)quinazoline (0.6 g), triethylamine (0.203 g) and DMF (2 ml). The mixture was stirred at ambient temperature for 4 hours. The mixture was evaporated and the residue was purified by column chromatography using increasingly polar mixtures of methylene chloride and ethyl acetate as eluent. There was thus obtained an oil which was triturated under a mixture of hexane and diethyl ether to give 4-(3'-methylanilino)-6-methylthiomethylquinazoline (0.205 g), m.p. 134°-136° C.

Aufarbeitung

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography
  3. temperatureusing increasingly polar mixtures of methylene chloride and ethyl acetate as eluent
  4. customThere was thus obtained an oil which
  5. customwas triturated under a mixture of hexane and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e7e1ea89a0024cd29cc31f550f81792d
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616582

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