HCID 19866789, compound → HCID 14793296, compound

To a suspension of lithium aluminum hydride (3.12 g, 82.2 mmol) in refluxing tetrahydrofuran under argon was added diamide 6 (3.50 g, 16.0 mmol) in small portions over 1 hour period. The mixture was refluxed for 3 days. After cooling to room temperature the excess reagent was destroyed by adding a mixture of water (2.7 ml) and THF (6.2 ml), then 15% aqueous NaOH (3.4 ml) and another mixture of water (5.6 ml) and THF (3.4 ml). The solid was filtered and washed extensively with pure THF. The filtrate and washings were combined, the solvent was removed in vacuo and the residue was chromatographed through a short alumina column with chloroform and the product was recrystallized from a chloroform-hexane mixture to give 1.88 g (62%) of 1-oxa-7-thia-4,10-diazacyclododecane (7) as a white solid mp 74°-76° C. Analysis calculated for C8H18N2OS: C, 50.49; H, 9.53. Found: C, 50.18; H, 9.72%.

1. temperatureThe mixture was refluxed for 3 days
2. customwas destroyed
3. additionby adding
4. additiona mixture of water (2.7 ml) and THF (6.2 ml)
5. addition15% aqueous NaOH (3.4 ml) and another mixture of water (5.6 ml) and THF (3.4 ml)
6. filtrationThe solid was filtered
7. washwashed extensively with pure THF
8. customthe solvent was removed in vacuo
9. customthe residue was chromatographed through a short alumina column with chloroform
10. customthe product was recrystallized from a chloroform-hexane mixture

ORD record

ord-5166af28132c4fb5aa8bcb724fa8c063

Source dataset

uspto-grants-1990_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04900818