Nitrogen → 5,7-Dichloro-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

In a 1 L 2-neck RBF equipped with mechanical stir, condenser and N2 inlet, C1 (42.5 g, 0.189 mol) was suspended into 400 mL of toluene. To this was added N,N-dimethylanaline (45.5 g. 0.375 mol) followed by the addition of POCl3 (29 g, 0.189 mol) and the reaction mixture stirred for 3 minutes at room temperature (RT). Reaction flask was placed in a 90° C. oil bath and the reaction mixture stirred/heated for 7 h and then at RT for 9 h. The reaction was quenched by adding 500 mL of ice water and stirred for 15 min. Organic layer was separated and quickly washed with cold 0.5 M HCl (300 mL), cold water (300 mL), and then cold saturated NaHCO3 (300 mL). Organic layer was dried (MgSO4), filtered and concentrated on a rotary evaporator to give 40 g of yellow solid. Yield 87.5%. 1H NMR (300 MHz, DMSO-d6) δ 3.25 (s, 3H), 3.8-3.9 (s, 1H, br), 4.3-4.4 (s, 1H, br), 7.4 (d, 1H), 7.7-7.8 (m, 2H).

1. additionTo this was added N,N-dimethylanaline (45.5 g. 0.375 mol)
2. customReaction flask
3. customwas placed in a 90° C.
4. temperaturethe reaction mixture stirred/heated for 7 h
5. waitat RT for 9 h
6. customThe reaction was quenched
7. additionby adding 500 mL of ice water
8. stirringstirred for 15 min
9. customOrganic layer was separated
10. washquickly washed with cold 0.5 M HCl (300 mL), cold water (300 mL)
11. dry with materialOrganic layer was dried (MgSO4)
12. filtrationfiltered
13. concentrationconcentrated on a rotary evaporator

ORD record

ord-448a5288475a4085bdcc361e522e9756

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759340B2