Hydrochloric Acid → HCID 54173930, compound

HRID 1448645Notes

Reaction equation

HRID 1448645 reaction equation
[NH2:1][CH:2]([CH2:5][CH3:6])[CH2:3][CH3:4].Cl[C:8]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:11]([CH2:12][O:13][CH2:14][CH2:15][OH:16])=[C:10]([CH3:22])[C:9]=1[N+:23]([O-:25])=[O:24].Cl>C1(C)C=CC=CC=1>[CH2:3]([CH:2]([NH:1][C:8]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][C:11]([CH2:12][O:13][CH2:14][CH2:15][OH:16])=[C:10]([CH3:22])[C:9]=1[N+:23]([O-:25])=[O:24])[CH2:5][CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 120193-PentanamineHCID 20380614HCID 20380614, compound

Product 1

HCID 54173930HCID 54173930, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Aminopentane (1.74 g; 0.02 mol) is added to a solution of 2-(4-chloro-2-methyl-3,5-dinitrobenzyloxy)ethanol (0.5 g; 1.7×10-3 mol) in toluene. The reaction mixture is heated at reflux for 3 hours. Analysis by tlc (silica gel plate; eluent: methanol-benzene in a 1:9 ratio) shows the reaction to be complete. The reaction mixture is poured into 10% hydrochloric acid and extracted with methylene chloride. The organic phase is dried over calcium sulfate; and evaporated in vacuo to afford 0.54 g (91.8%) of an orange-colored oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 3 hours
  3. customthe reaction
  4. extractionextracted with methylene chloride
  5. dry with materialThe organic phase is dried over calcium sulfate
  6. customand evaporated in vacuo

Sources & evidence

ORD record
ord-ed6756788d104a1aa5b33f2b9760dc15
Source dataset
uspto-grants-1979_12
Patent number
US04180679

Reaction notes

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