Acetyl chloride → 1,3,5-Triazino(1,2-a)benzimidazol-4(3H)-one, 10-acetyl-2,10-dihydro-2,2,3-trimethyl-

HRID 615090Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 615090
[CH3:1][C:2]1([CH3:17])[N:10]([CH3:11])[C:9](=[O:12])[N:8]2[C:4](=[N:5][C:6]3[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=32)[NH:3]1.[C:18](Cl)(=[O:20])[CH3:19].Cl.C([NH+](CC)CC)C.[NH4+].[OH-]>CO.C(Cl)(Cl)Cl.C(N(CC)CC)C.CC(C)=O>[C:18]([N:5]1[C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2[N:8]2[C:9](=[O:12])[N:10]([CH3:11])[C:2]([CH3:17])([CH3:1])[N:3]=[C:4]12)(=[O:20])[CH3:19]

Komponenten

9

Edukt 4

HCID 6367Acetyl chlorideHCID 14923Ammonium HydroxideHCID 1591201,2-dihydro-2,2,3-trimethyl-1,3,5-triazino[1,2-a]benzimidazol-4(3H)-oneHCID 21900368Triethylammonium hydrochloride

Produkt 1

HCID 1591101,3,5-Triazino(1,2-a)benzimidazol-4(3H)-one, 10-acetyl-2,10-dihydro-2,2,3-trimethyl-Ausbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittelHCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A 250-ml, round-bottomed flask containing a magnetic stirring bar was charged with 2.45 g (0.0106 mole) of 1,2-dihydro-2,2,3-trimethyl-1,3,5-triazino[1,2-a]benzimidazol-4-(3H)-one, 150 ml of acetone and 1.53 ml of triethylamine. Acetyl chloride (0.86 g, 0.0110 mole) was added rapidly via syringe to the resulting solution. The mixture was stirred for two hours at room temperature after which time a white precipitate of triethylammonium hydrochloride was visible. Examination of the reaction mixture by TLC (silica, 80:2:1, CHCl3 : CH3OH: NH4OH) showed that only a trace of starting material remained. The mixture was concentrated in vacuo and the resulting solid was taken up in methylene chloride. The resulting solution was washed with water (3 times) brine, dried (MgSO4) and concentrated under reduced pressure to afford 1.5 g (52% yield) of a white solid which was analytically pure, mp 159°-62° C.

Aufarbeitung

  1. additionA 250-ml, round-bottomed flask containing a magnetic stirring bar
  2. concentrationThe mixture was concentrated in vacuo
  3. washThe resulting solution was washed with water (3 times) brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f022793528184ecaaac2705f4a4ba12d
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04497650

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