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

HRID 1460809Notes

Reaction equation

HRID 1460809 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 resultant mixture was refluxed for 4 hours. After cooling the reaction mixture, the solvent was distilled off and the residue formed was dissolved in chloroform. To the solution formed 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. 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 removing inorganic matters by filtration from the organic phase, the solvent was distilled from the organic phase and the residue was recrystallized from a 1:3 mixture of acetonitrile and methanol to provide 186 g of the above-described compound with a yield of 76.0%. The melting point thereof was 55° C. to 56° C.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. distillationthe solvent was distilled off
  3. customthe residue formed
  4. customTo the solution formed
  5. additionwas added to the reaction mixture
  6. customthe organic phase thus formed
  7. customwas recovered
  8. dry with materialdried over anhydrous sodium sulfate
  9. customAfter removing inorganic matters
  10. filtrationby filtration from the organic phase
  11. distillationthe solvent was distilled from the organic phase
  12. customthe residue was recrystallized from a 1:3 mixture of acetonitrile and methanol

Sources & evidence

ORD record
ord-d42b7d8ea6274af08e7bb1aac79b5d17
Source dataset
uspto-grants-1991_12
Patent number
US05071994

Reaction notes

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