Chloride → 3-chloro,4-methyl-N,N-di-sec.butyl-benzamide

HRID 1576828Notes

Reaction equation

HRID 1576828 reaction equation
[Cl-].[Cl:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([OH:8])=O.[CH:13]([NH:17][CH:18]([CH2:20][CH3:21])[CH3:19])([CH2:15][CH3:16])[CH3:14]>C1C=CC=CC=1.C(N(CC)CC)C>[Cl:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:6]([N:17]([CH:18]([CH2:20][CH3:21])[CH3:19])[CH:13]([CH2:15][CH3:16])[CH3:14])=[O:8]

Participants

6

Reactant 3

HCID 312ChlorideHCID 12277DI-Sec-butylamineHCID 788403-Chloro-4-methylbenzoic Acid

Product 1

HCID 215093873-chloro,4-methyl-N,N-di-sec.butyl-benzamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8471TriethylamineSolvent

Procedure

To these 17.9 g of the chloride of 3-chloro,4-methylbenzoic acid, dissolved in 60 ml of anhydrous benzene, were added 12.9 g of di-sec.butylamine dissolved in 15 ml of anhydrous C6H 6 and 12.3 g of triethylamine. The whole was then boiled to reflux temperature for 1 hour and was then left to cool down to room temperature. The reaction mass was then concentrated to dryness under reduced pressure. The residue was washed with acidulated H2O, with H2O and extracted with ethyl ether. The etheral extract was dried on anhydrous Na 2 SO4, filtered, and the solvent was then removed by reduced pressure. The oily residue was fractionally distilled at a pressure of 0.05 mm Hg. The fraction which passed over at 143°-144°C was collected. Thereby were obtained 26.5 g of 3-chloro,4-methyl-N,N-di-sec.butyl-benzamide.

Workup

  1. temperatureto reflux temperature for 1 hour
  2. waitwas then left
  3. concentrationThe reaction mass was then concentrated to dryness under reduced pressure
  4. washThe residue was washed with acidulated H2O, with H2O
  5. extractionextracted with ethyl ether
  6. extractionThe etheral extract
  7. dry with materialwas dried on anhydrous Na 2 SO4
  8. filtrationfiltered
  9. customthe solvent was then removed by reduced pressure
  10. distillationThe oily residue was fractionally distilled at a pressure of 0.05 mm Hg
  11. custompassed over at 143°-144°C
  12. customwas collected

Sources & evidence

ORD record
ord-506a605cbcc841a7884e34cdfa0fe6fa
Source dataset
uspto-grants-1976_09
Patent number
US03982931

Reaction notes

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