Diethyl Ether → Diisopropylether ethyl acetate

HRID 1058503Notes

Reaction equation

HRID 1058503 reaction equation
ClC1C([N+]([O-])=O)=CC([N+]([O-])=O)=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH3:17]NCCN1CC[O:24][CH2:23][CH2:22]1.CC[O:29][CH2:30][CH3:31]>O>[CH3:22][CH2:23][O:24][C:7]([CH3:6])=[O:8].[O:29]([CH:6]([CH3:7])[CH3:10])[CH:30]([CH3:31])[CH3:17]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11471076HCID 11471076, compoundHCID 14979282Methyl(2-(morpholin-4-yl)ethyl)amine

Product 1

HCID 22281796Diisopropylether ethyl acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Similar reaction of crude 5-chloro-2,4-dinitrobenzoyl chloride in Et2O with 4-[2-(methylamino)ethyl]morpholine (2 equiv) in water, followed by chromatography of the product on alumina-90, eluting with EtOAc, gave 5-chloro-N-methyl-N-[2-(4-morpholino)ethyl]-2,4-dinitrobenzamide (48%), mp (EtOAc/iPr2O) 123-123.5° C. 1H NMR [(CD3)2SO] [rotamer mixture] δ8.94 & 8.94 (2xs, 1H, H-3), 8.13 & 8.09 (2xs, 1H, H-6), [3.63-3.54 (m), 3.51, t (J=4.6 Hz) & 3.28-3.18(m), 6H, O(CH2)CH2, N(CH3)CH2], 3.05 & 2.89 (2xs, 3H, CH3), [2.57 (t, J=6.6 Hz), 2.50-2.38 (m) & 2.25 (t, J=4 3 Hz), 6H, CH2N(CH2)CH2]. Anal. Calcd. for C14H17ClN4O6: C, 45.11,H, 4.60; N, 15.03. Found: C, 45.01;H, 4,43, N, 15.02%.

Workup

  1. washeluting with EtOAc

Sources & evidence

ORD record
ord-306897965aa74207afc0312a9027de98
Source dataset
uspto-grants-2003_02
Patent number
US06517836B1

Reaction notes

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