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

HRID 728525Notes

Reaction equation

HRID 728525 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[Cl:13])[C:7]([OH:9])=O)([O-:3])=[O:2].C(#N)C.S(Cl)(Cl)=O.[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]>O.C(Cl)(Cl)Cl.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:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:12]([Cl:13])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=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 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

102.7 g of 3-nitro-4-chlorobenzoic acid was mixed with 800 ml of acetonitrile, and thereto was added 68.6 g of thionyl chloride. The resulting mixture was heated under reflux for 4 hours, and thereto was added 63.5 g of triethylamine. After controlling the temperature of the reaction system to 5° C., a chloroform solution containing 148.6 g of methyloctadecylamine was further added dropwise. After the completion of the reaction, the reaction mixture was dispersed into water, and the organic phase was dried over anhydrous sodium sulfate. The inorganic matter was filtered out, and the solvent was distilled away. The reaction product was recrystallized from a 1:3 mixture of acetonitrile and methanol. Yield: 186 g, Percent yield: 76.0%, Melting point: 55°-56° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customto 5° C.
  4. additionwas further added dropwise
  5. customAfter the completion of the reaction
  6. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  7. filtrationThe inorganic matter was filtered out
  8. distillationthe solvent was distilled away
  9. customThe reaction product was recrystallized from a 1:3 mixture of acetonitrile and methanol

Sources & evidence

ORD record
ord-c330a734d1804dda9e577e76f6c41067
Source dataset
uspto-grants-1991_09
Patent number
US05049477

Reaction notes

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