Dinitrofluorobenzene → HCID 15115611, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL round bottom flask fitted with a magnetic stirrer was charged with 221.1 mg (1.0 mmol) of 1,6 diamino-3,4-dihydrox-yhexane dihydrochloride, 409 mg (2.2 mmol) of 2,4-dinitrofluorobenzene, 130 mg (0.94 mmol) of K2CO3 and 10 mL of H2O. The mixture was stirred at 75° C. for 5 h. After cooling the yellow precipitate was isolated by filtration, washed with H2O and dried, affording 310 mg of crude product. This material (46 mg) was recrystallized from 2 mL of 1:1 H2O/DMF affording 20.4 mg of N,N'-bis(2,4-dinitrophenyl)-1,6 diamino-3,4-dihydroxy-hexane, mp 199° C. dec. Calcd for C18H20N6O10 : C, 45.00; H, 4.17; N, 1750. Found: C, 44.68; H, 4.19; N, 17.12. 200 MHz NMR (acetone-d6): 1.9 (m, 2H), 2.15 (m, 2H), 3.78 (m, 6H), 4.34 (d, J =4.8 Hz, 2H, active H), 7.30 (d, J=9.6, 2H), 8.30 (dd, J =2.2, 9.6, 2H), 8.99 (d, J=2.6 Hz, 2H), 9.1 (m, 1H).

Provenance & Evidence