Acetonitrile → 4-Chloro-N-methyl-3-nitro-N-octadecylbenzamide

HRID 1588384Notes

Reaction equation

HRID 1588384 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[Cl:17])[C:11]([OH:13])=O)([O-:7])=[O:6].C(#N)C.[CH3:21][NH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>C(Cl)(Cl)Cl.O.C(N(CC)CC)C>[CH3:21][N:22]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:11](=[O:13])[C:10]1[CH:14]=[CH:15][C:16]([Cl:17])=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 73204-Chloro-3-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 75539N-Methyloctadecylamine

Product 1

HCID 143236474-Chloro-N-methyl-3-nitro-N-octadecylbenzamideYield 76%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

After adding 68.6 g of thionyl chloride to a mixture of 105.7 g of 3-nitro-4-chlorobenzoic acid and 800 ml of acetonitrile, the mixture was refluxed for 4 hours. After cooling the reaction mixture, the solvent was distilled off therefrom and the residue formed was dissolved in chloroform. To the solution was added 63.5 g of triethylamine and after adjusting the temperature thereof to 5° C., a chloroform solution of 148.6 g of N-methyloctadecylamine was added dropwise to the solution to perform reaction. After the reaction was over, water was added to the reaction mixture, and the organic phase thus formed was recovered and dried over anhydrous sodium sulfate. After filtering off inorganic materials, the solvent was distilled off from the filtrate and the residue was recrystallized from a 1:3 mixture of acetonitrile and methanol to provide 186 g of the desired compound with a yield of 76.0%. The melting point thereof was 55° C. to 56° C.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. temperatureAfter cooling the reaction mixture
  3. distillationthe solvent was distilled off
  4. customthe residue formed
  5. customreaction
  6. additionwas added to the reaction mixture
  7. customthe organic phase thus formed
  8. customwas recovered
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationAfter filtering off inorganic materials
  11. distillationthe solvent was distilled off from the filtrate
  12. customthe residue was recrystallized from a 1:3 mixture of acetonitrile and methanol

Sources & evidence

ORD record
ord-8521c15ff0ad4e54a4fbc23d1819cdb9
Source dataset
uspto-grants-1993_06
Patent number
US05221750

Reaction notes

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