1-[3-(Dimethylamino)propyl]piperazine → 2-{2-[4-(3-Dimethylaminopropyl)-1-piperazinyl]-5-thiadiazolyl}-1-methyl-5-nitroimidazole

HRID 462236

Reaction equation

HRID 462236 reaction equation
Cl[N:2]1[NH:6][CH:5]=[C:4]([C:7]2[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=2)[S:3]1.[CH3:16][N:17]([CH3:27])[CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>O1CCOCC1>[CH3:27][N:17]([CH3:16])[CH2:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][N:24]([N:2]2[NH:6][CH:5]=[C:4]([C:7]3[N:8]([CH3:15])[C:9]([N+:12]([O-:14])=[O:13])=[CH:10][N:11]=3)[S:3]2)[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 27362341-[3-(Dimethylamino)propyl]piperazineHCID 21390801HCID 21390801, compound

Product 1

HCID 213908032-{2-[4-(3-Dimethylaminopropyl)-1-piperazinyl]-5-thiadiazolyl}-1-methyl-5-nitroimidazole

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2-(2-chloro-5-thiadiazolyl)-1-methyl-5-nitroimidazole in 200 ml. of dioxane is treated with 5.1 g. of 1-(3-dimethylaminopropyl)piperazine, and the mixture stirred at room temperature for 18 hours. The precipitate is collected, dissolved in 100 ml. of water, made alkaline with sodium hydroxide solution, and then extracted with 500 ml. of chloroform. The chloroform extract is dried and the solvent removed under reduced pressure. The yellow residue is recrystallized from 100 ml. of ethanol to give 2.9 g. of product, melting at 174°-175° C.

Workup

  1. customThe precipitate is collected
  2. dissolutiondissolved in 100 ml
  3. extractionextracted with 500 ml
  4. extractionThe chloroform extract
  5. customis dried
  6. customthe solvent removed under reduced pressure
  7. customThe yellow residue is recrystallized from 100 ml
  8. customof ethanol to give 2.9 g

Sources & evidence

ORD record
ord-c2bace9bd66849a0a94a28186d1478c3
Source dataset
uspto-grants-1977_12
Patent number
US04065567

Linked notes

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