Diisopropylethylamine → 3,3,9,9-Tetramethyl-1-(4-methyl-2-nitro-1H-imidazol-1-yl)-4,8-diazaundecane-2,10-dione dioxime

HRID 968161Notes

Reaction equation

HRID 968161 reaction equation
Cl[C:2]([CH3:17])([CH3:16])[CH:3]([N:14]=[O:15])[CH2:4][N:5]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]1[N+:11]([O-:13])=[O:12].[NH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([CH3:30])([CH3:29])[C:24](=[N:27][OH:28])[CH2:25]C.CCN(C(C)C)C(C)C>C(#N)C>[CH3:16][C:2]([CH3:17])([NH:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]([CH3:30])([CH3:29])[C:24](=[N:27][OH:28])[CH3:25])[C:3](=[N:14][OH:15])[CH2:4][N:5]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 151859953-Chloro-3-methyl-2-nitroso-1-(4-methyl-2-nitro-1H-imidazol-1-yl)butaneHCID 86585151N-(3-aminopropyl)-1-amino-1,1-dimethyl-2-butanone oxime

Product 1

HCID 850650873,3,9,9-Tetramethyl-1-(4-methyl-2-nitro-1H-imidazol-1-yl)-4,8-diazaundecane-2,10-dione dioxime

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

3-Chloro-3-methyl-2-nitroso-1-(4-methyl-2-nitro-1H-imidazol-1-yl)butane (3.41 g, 13.09 mmol) was added in portions to a stirred solution of N-(3-aminopropyl)-1-amino-1,1-dimethyl-2-butanone oxime (2.0 g, 11.56 mmol, Example 1) and (i-Pr)2NEt (1.64 g, 13.09 mmol) in dry acetonitrile (20 mL) at 50° C. under a nitrogen atmosphere. After the addition the reaction mixture was stirred for an additional 2 hours at 50° C. and cooled to room temperature. The solid which formed was filtered and recrystallized from acetonitrile to provide the title product as a light yellow colored solid.

Workup

  1. additionAfter the addition the reaction mixture
  2. temperaturecooled to room temperature
  3. customThe solid which formed
  4. filtrationwas filtered
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-4ab0b8a1598c4553ba700521b0b53c5c
Source dataset
uspto-grants-2005_10
Patent number
US06958141B2

Reaction notes

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