Phosgene → 4-Chloro-6-(4-isocyanato-phenoxy)-pyrimidine

Apparatus: 2 litre 3-neck-roundbottle flask, dropping funnel, short Vigreux column and condenser. A phosgene solution (20% in toluene, 118 ml; 223 mmol) diluted with toluene (800 ml) under N2-atmosphere is cooled to approximately −20° C. Then a solution of 4-(6-chloro-pyrimidin-4-yl-oxy)-aniline (Stage 21.1; 18.52 g, 83.6 mmol) in CH2Cl2 (400 ml) is added dropwise. The resulting suspension is heated to distil off approximately 400 ml of solvent. Distillation Is continued (boiling point: 110° C.), while a mixture of phosgene solution (20% in toluene, 59 ml) and toluene (500 ml) is added dropwise, followed by toluene (250 ml). The resulting clear solution (a 250 ml) in the reaction vessel is cooled to rt, filtered and the filtrate concentrated in vacuo. Distillation of the resulting waxy crude product on the Kugelrohr apparatus (0.2 mbar, 200° C.) gives the title compound as a solid: m.p.: 103° C.; MS: [M+1]+=302; 1H-NMR (CDCl3): 8.57 (s, 1H), 7.17 (d, 2H), 7.10 (d, 2H), 6.95 (s, 1H).

1. customApparatus: 2 litre 3-neck-roundbottle flask, dropping
2. temperatureThe resulting suspension is heated
3. customto distil off approximately 400 ml of solvent
4. distillationDistillation
5. additionwhile a mixture of phosgene solution (20% in toluene, 59 ml) and toluene (500 ml)
6. additionis added dropwise
7. temperatureThe resulting clear solution (a 250 ml) in the reaction vessel is cooled to rt
8. filtrationfiltered
9. concentrationthe filtrate concentrated in vacuo
10. distillationDistillation of the resulting waxy crude product on the Kugelrohr apparatus (0.2 mbar, 200° C.)

ORD-Eintrag

ord-ef01c83b58694077b2eada6eafe64fc8

Quelldatensatz

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07652022B2