Potassium → N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-acenaphthene-1,2-dicarboximide

HRID 1973448

Reaction equation

HRID 1973448 reaction equation
[CH:1]12[C:15](=[O:16])[NH:14][C:13](=[O:17])[CH:2]1[C:3]1[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]2=3)[CH:6]=[CH:5][CH:4]=1.[K].S(C1C=CC(C)=CC=1)(O)(=O)=O.O[CH2:31][CH2:32][N:33]1[C:37]([N+:38]([O-:40])=[O:39])=[CH:36][N:35]=[C:34]1[CH3:41]>O>[CH3:41][C:34]1[N:33]([CH2:32][CH2:31][N:14]2[C:13](=[O:17])[CH:2]3[C:3]4[C:12]5[C:7](=[CH:8][CH:9]=[CH:10][C:11]=5[CH:1]3[C:15]2=[O:16])[CH:6]=[CH:5][CH:4]=4)[C:37]([N+:38]([O-:40])=[O:39])=[CH:36][N:35]=1

Participants

5

Reactant 3

HCID 5462222PotassiumHCID 21491653Acenaphthene-1,2-dicarboximideHCID 867342581-(2-Hydroxyethyl)-2-methyl-5-nitroimidazole tosylate

Product 1

HCID 21491671N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-acenaphthene-1,2-dicarboximide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acenaphthene-1,2-dicarboximide is converted to the potassium salt and reacted with 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole tosylate according to the procedure described in Example 13. The crude reaction mixture is cooled and diluted with water, and then extracted with toluene. The solvent is evaporated from the toluene extract and the residue recrystallized from ethanol to give N-[2-(2-methyl-5-nitro-1-imidazolyl)ethyl]-acenaphthene-1,2-dicarboximide melting at about 183°-185° C.

Workup

  1. customThe crude reaction mixture
  2. temperatureis cooled
  3. extractionextracted with toluene
  4. customThe solvent is evaporated from the toluene
  5. extractionextract
  6. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-89f21b68d4a7411f94b4a050c9f0a229
Source dataset
uspto-grants-1976_12
Patent number
US03997572

Linked notes

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