Formic Acid → 5,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-one

Reaktionsgleichung

[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]#[N:12].[CH:13](O)=O.Cl.[OH2:17]>>[N:1]1[C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=3[C:3]=2[C:11](=[O:17])[NH:12][CH:13]=1

Komponenten

Edukt 4

HCID 284Formic Acid

HCID 313Hydrochloric Acid

HCID 962Water

HCID 783822-Amino-4,5,6,7-tetrahydrobenzo(b)thiophene-3-carbonitrile

Produkt 1

HCID 986145,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-oneAusbeute 77 %

Versuchsvorschrift

To a mixture of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl cyanide (0.9 g) and formic acid (10 mL) was added 0.1 mL conc. HCl. After refluxed for 16 h, the reaction mixture was cooled and water (20 mL) was added. The precipitate was collected by filtration and washed thoroughly with water and hexanes to give the title compound (0.8 g, 77%). 1H NMR (300 MHz, CDCl3): δ 7.91 (s, 1H), 3.03-3.00 (m, 2H), 2.80-2.77 (m, 2H), 1.89-1.83 (m, 4H).