Diisopropyl Ether → 5-Methylbenzimidazolone

HRID 1503225

Reaktionsgleichung

Reaktionsgleichung von HRID 1503225
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[C:10](N1C=CN=C1)(N1C=CN=C1)=[O:11].C(OC(C)C)(C)C>O1CCCC1.ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:10](=[O:11])[NH:9][C:4]=2[CH:3]=1

Komponenten

6

Edukt 3

HCID 7914Diisopropyl EtherHCID 103323,4-DiaminotolueneHCID 682631,1'-Carbonyldiimidazole

Produkt 1

HCID 2231345-MethylbenzimidazoloneAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-methyl-1,2-phenylenediamine (1) (25 g) in tetrahydrofuran (375 mL) was added dropwise a solution of 1,1′-carbonyldiimidazole (36.5 g) in dichloromethane (375 mL). After stirring at room temperature for 6.5 hr, diisopropylether (375 mL) was added to the reaction mixture. After stirring at room temperature, the resulting precipitate was collected by filtration. The precipitate was washed with diisopropyl ether, and dried under reduced pressure to give 5-methyl-1,3-dihydrobenzimidazol-2-one (2) (24.6 g).

Aufarbeitung

  1. stirringAfter stirring at room temperature
  2. filtrationthe resulting precipitate was collected by filtration
  3. washThe precipitate was washed with diisopropyl ether
  4. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5d4a4d46e4d341b2ad72b1f0468b94d1
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09212169B2

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