Dinitrofluorobenzene → HCID 15115611, compound

HRID 704544Notes

Reaction equation

Cl.Cl.[NH2:3][CH2:4][CH2:5][CH:6]([OH:12])[CH:7]([OH:11])[CH2:8][CH2:9][NH2:10].[N+:13]([C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1F)([O-:15])=[O:14].C([O-])([O-])=O.[K+].[K+]>O>[N+:13]([C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[NH:3][CH2:4][CH2:5][CH:6]([OH:12])[CH:7]([OH:11])[CH2:8][CH2:9][NH:10][C:17]1[CH:18]=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:16]=1[N+:13]([O-:15])=[O:14])([O-:15])=[O:14]

Participants

Conditions

Temperature: 75 °C

Procedure

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).

Workup

customA 25 mL round bottom flask fitted with a magnetic stirrer
temperatureAfter cooling the yellow precipitate
customwas isolated by filtration
washwashed with H2O
customdried

Sources & evidence

ORD record: ord-0a0c08a6de5f4db8874eff4a1aba1091
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04988625

Reaction notes

Loading…