N-Methylbutylamine → N-(2-nitrophenyl)-2-(N-n-butyl-N-methylamino)acetamide

HRID 1415644Notes

Reaction equation

HRID 1415644 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:14])[CH2:12]Cl)([O-:3])=[O:2].[CH2:15]([NH:19][CH3:20])[CH2:16][CH2:17][CH3:18]>C1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11](=[O:14])[CH2:12][N:19]([CH2:15][CH2:16][CH2:17][CH3:18])[CH3:20])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 8068N-MethylbutylamineHCID 2224432-chloro-N-(2-nitrophenyl)acetamide

Product 1

HCID 21482991N-(2-nitrophenyl)-2-(N-n-butyl-N-methylamino)acetamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-(2-Nitrophenyl)-2-chloroacetamide (32.2 g) was dissolved in benzene (350 ml) and N-n-butylmethylamine (26.1 g) added. The mixture was boiled under reflux for 22 hours, the benzene evaporated off, and water (300 ml) added. The mixture was extracted with diethyl ether (3 × 200 ml), the extract dried with magnesium sulphate, filtered, and the ether evaporated off to give N-(2-nitrophenyl)-2-(N-n-butyl-N-methylamino)acetamide as a yellow oil which was used in the next stage without purification.

Workup

  1. temperatureunder reflux for 22 hours
  2. customthe benzene evaporated off
  3. additionwater (300 ml) added
  4. extractionThe mixture was extracted with diethyl ether (3 × 200 ml)
  5. dry with materialthe extract dried with magnesium sulphate
  6. filtrationfiltered
  7. customthe ether evaporated off

Sources & evidence

ORD record
ord-f245d71673294dfe91aed627a82039a0
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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