Diisopropyl Ether → HCID 10220113, compound

HRID 1595006Notes

Reaction equation

HRID 1595006 reaction equation
[C:1](ON=O)([CH3:4])([CH3:3])[CH3:2].BrCC(C)=C.[N+:13]([C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)N)([O-:15])=[O:14].C(OC(C)C)(C)C>CC#N>[CH3:4][C:1](=[CH2:2])[CH2:3][C:18]1[CH:17]=[C:16]([N+:13]([O-:15])=[O:14])[CH:22]=[C:21]([N+:23]([O-:25])=[O:24])[CH:20]=1

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 10906Tert-Butyl nitriteHCID 120683,5-DinitroanilineHCID 3577853-Bromo-2-methyl-1-propene

Product 1

HCID 10220113HCID 10220113, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of t-butylnitrite (0.13 ml, 1.1 mmol) and 3-bromo-2-methylpropene (0.82 ml, 8.25 mmol) in 1 ml CH3CN, 3,5-dinitroaniline (0.10 g, 0.55 mmol) was added at room temperature. The solution was stirred for 17 h at room temperature and then isopropylether was added. The suspension was filtered through a pad of Al2O3. The volatile material in the solution was removed at reduced pressure to give the title compound. 1H-NMR (CDCl3, 300 MHz) δ ppm: 8.92 (t, J=2.1 Hz, 1H), 8.40 (d, J=2.1 Hz, 2H), 5.00 (s, 1H), 4.82 (s, 1H), 3.55 (s, 2H), 1.72 (s, 3H). 13C-NMR (CDCl3, 75.43 MHz) δ ppm: 148.4, 144.2, 142.0, 129.0, 116.9, 114.8, 43.9, 22.0.

Workup

  1. filtrationThe suspension was filtered through a pad of Al2O3
  2. customThe volatile material in the solution was removed at reduced pressure

Sources & evidence

ORD record
ord-8290b514611a4a279456410e51c327d9
Source dataset
uspto-grants-2001_09
Patent number
US06284894B1

Reaction notes

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