Phosgene → HCID 19104097, compound

A 60% NaH/mineral oil dispersion (100 mg, 2.61 mmol) was washed with hexane and suspended in THF (1.0 mL). 1-isopropyl-1,3-dihydro-2H-benzimidazol-2-one (115 mg, 0.653 mmol) was added to the suspension. This mixture was stirred for 15 minutes before adding it to a mixture of 2.38 mL (5.22 mmol) of 20% phosgene (toluene)/2.6 mL THF. The resulting mixture was stirred for 2.5 hours, filtered through celite, and concentrated. The residue was redissolved in THF (2.0 mL) and the amine of Example 11J (166 mg, 0.653 mmol) was added with triethylamine (0.137 mL, 0.98 mmol). This mixture was stirred for 18 hours and then concentrated to dryness. The residue was dissolved in chloroform, washed with saturated aqueous K2CO3, water, and then dried over K2CO3. Filtration and concentration afforded an oil. Purification by chromatography on silica gel eluting with 5% methanol(NH3)/chloroform gave 86 mg (27%) of the title compound.

1. washA 60% NaH/mineral oil dispersion (100 mg, 2.61 mmol) was washed with hexane
2. additionbefore adding it
3. stirringThe resulting mixture was stirred for 2.5 hours
4. filtrationfiltered through celite
5. concentrationconcentrated
6. dissolutionThe residue was redissolved in THF (2.0 mL)
7. stirringThis mixture was stirred for 18 hours
8. concentrationconcentrated to dryness
9. dissolutionThe residue was dissolved in chloroform
10. washwashed with saturated aqueous K2CO3, water
11. dry with materialdried over K2CO3
12. filtrationFiltration and concentration
13. customafforded an oil
14. customPurification by chromatography on silica gel eluting with 5% methanol(NH3)/chloroform

ORD record

ord-55ade165658b408bbccb3cd0cec6ba41

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05521193