Diethanolamine → Ethanol, 2,2'-((4-nitrophenyl)imino)bis-

HRID 1873615Notes

Reaction equation

HRID 1873615 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[NH:11]([CH2:15][CH2:16][OH:17])[CH2:12][CH2:13][OH:14]>CO.ClCCl>[OH:14][CH2:13][CH2:12][N:11]([C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1)[CH2:15][CH2:16][OH:17]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 9590p-Fluoronitrobenzene

Product 1

HCID 87515Ethanol, 2,2'-((4-nitrophenyl)imino)bis-Yield 85%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-fluoronitrobenzene (5 g, 35 mmol) and diethanolamine (7.5 g, 71 mmol) was heated to 130° C. without solvent for 4 hours. The crude reaction mixture after chromatography on silica gel (gravity, methanol:dichloromethane 1:19 then 1:9) gave the title compound (6.7 g, 85% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.98 (d, 2H), 6.78 (d, 2H), 4.83 (t, 2H), 3.50-3.65 (m, 8H). 13C NMR (75 MHz, DMSO-d6) δ 154.36, 136.16, 126.77, 111.66, 58.89, 54.17. Mass spectrum m/z 227 (MH+). Anal. calcd. for C10H14N2O4 C, 53.09; H, 6.24; N, 12.38. Found C, 53.09; H, 6.32; N, 12.34.

Sources & evidence

ORD record
ord-240e7cfd7a10427fa598e4cc019a2c9c
Source dataset
uspto-grants-2012_11
Patent number
US08304409B2

Reaction notes

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