Diethanolamine → HCID 642072, compound

HRID 1290331Notes

Reaction equation

HRID 1290331 reaction equation
Cl[C:2]1[C:3]([N+:15]([O-:17])=[O:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[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:3]([N+:15]([O-:17])=[O:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[CH2:22][CH2:23][OH:24]

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 4524946HCID 4524946, compound

Product 1

HCID 642072HCID 642072, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 5-chloro-2,4-dinitrobenzoate (IV) (1.24 g, 4.76 mmol) was treated with diethanolarnine (1.00 g, 9.52 mmol) in dioxane (50 mL) at 50 ° C. for 3 h, and the residue after workup was chromatographed on silica gel. Elution with EtOAc gave methyl 5-[N,N-bis(2-hydroxyethyl)amino]-2,4-dinitrobenzoate (V) (1.52 g. 97%). mp (EtOAc/petroleum ether) 104°-106° C. 1H NMR (CDCl3) δ8.48 (s, 1 H, H-3), 7.45 (s, 1H, H-6), 3.95 (s, 3H, OCH3), 3.81 (t, J=5.0 Hz, 4 H, CH2OH), 3.60 (t,J=5.0 Hz, 4H, CH2N), 2.20 (br, 2H, OH). 13C NMR δ165.89 (COOMe), 147.53 (C-5), 138.67, 136.21 (C-2,4), 133.30 (C-1), 124.22. 121.65 (C-3,6), 59.34 (CH2OH), 54.59 (CH2N), 53.74 (OCH3). Anal. (C12H15N3O8) C,H,N.

Workup

  1. customthe residue after workup was chromatographed on silica gel
  2. washElution with EtOAc

Sources & evidence

ORD record
ord-fdf70e508b904d488ff47e76205fbba2
Source dataset
uspto-grants-1998_05
Patent number
US05750782

Reaction notes

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