Diethanolamine → HCID 10640062, compound

HRID 1899062Notes

Reaction equation

HRID 1899062 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[NH:18]([CH2:22][CH2:23][OH:24])[CH2:19][CH2:20][OH:21]>O1CCOCC1>[OH:21][CH2:20][CH2:19][N:18]([C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16])[CH2:22][CH2:23][OH:24]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 96161Methyl 4-chloro-3,5-dinitrobenzoate

Product 1

HCID 10640062HCID 10640062, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 4-chloro-3,5-dinitrobenzoate (XIV) (10.0 g, 0.036 mol) and diethanolamine (7.66 g, 0.073 mol) in p-dioxane (60 mL) was stirred at 50° C. for 5 h. Volatiles were removed under reduced pressure, and the residue was adsorbed directly onto silica gel and chromatographed. Elution with EtOAc/petroleum ether (1:10) gave foreruns, and subsequent elution with EtOAc/petroleum ether (3:2) gave methyl 4-[N,N-bis(2-hydroxyethyl)amino]-3,5-dinitrobenzoate (XV: X=OH, Z=OMe) (9.61 g, 80%), mp (CHCl3 /petroleum ether) 101°-103° C. 1H NMR (CDCl3) δ 8.52 (s, 2 H, ArH-2,6), 3.97 (s, 3 H, COOCH3), 3.76 (dxt, J=6.5, 4.7 Hz, 4 H, CH2OH), 3.26 (t, J=4.7 Hz, 4 H, NCH2), 2.76 (t, J=6.5 Hz, 2 H, OH). 13C NMR δ 163.14 (COOCH3), 145.50 (C-4), 142.54 (C-3,5), 131.19 (C-2,6), 123.59 (C-1), 59.16 (CH2OH)1, 54.58 (CH2N), 53.14 (OCH3). Anal. (C12H15N3O8) C,H,N.

Workup

  1. customVolatiles were removed under reduced pressure
  2. customchromatographed
  3. washElution with EtOAc/petroleum ether (1:10)
  4. customgave
  5. washforeruns, and subsequent elution with EtOAc/petroleum ether (3:2)

Sources & evidence

ORD record
ord-304446f840084a4697d3affd32c0778c
Source dataset
uspto-grants-1996_11
Patent number
US05571845

Reaction notes

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