Dichloromethane → 4-(2-Chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one

Reaktionsgleichung

[CH3:1][N:2]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[CH2:3]1.C(Cl)(Cl)=[O:17].C1(C)C=CC=CC=1.C(N(CC)CC)C.[CH2:34]([Cl:36])Cl>>[Cl:36][CH2:34][CH2:5][CH:4]1[C:7]2=[N:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]2[C:1](=[O:17])[N:2]([CH3:6])[CH2:3]1

Komponenten

Edukt 4

HCID 6344Dichloromethane2×

HCID 8471Triethylamine

HCID 19083224Phosgen toluene

HCID 199898622-(1-Methyl-3-pyrrolidinyl)-1H-benzimidazole

Produkt 1

HCID 199898454-(2-Chloroethyl)-3,4-dihydro-2-methylpyrimido[1,6-a]benzimidazol-1(2H)-one

Versuchsvorschrift

A solution of 4 g (0.02 mol) of 2-(1-methyl-3-pyrrolidinyl)-1H-benzimidazole in 100 mL of CH2Cl2 was added dropwise to a solution of 12.5 (0.025 mol) of 20% phosgene/toluene in 30 mL of CH2Cl2. The solution was stirred for 2 h, and 10 g (0.1 mol) of triethylamine was added dropwise. Stirring was continued for 2 h and the solution was extracted with dilute NaOH. The organic layer was dried (Na2SO4) and concentrated. The residue was crystallized twice from isopropyl ether. Yield 1.5 g (28%), mp 88°-91° C.