DI-Sec-butylamine → N,N-Di(butan-2-yl)-2,3,5-trichlorobenzamide

HRID 1576827Notes

Reaction equation

HRID 1576827 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[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:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4]([N:17]([CH:18]([CH2:20][CH3:21])[CH3:19])[CH:13]([CH2:15][CH3:16])[CH3:14])=[O:5]

Participants

5

Reactant 2

HCID 12277DI-Sec-butylamineHCID 130111162,3,5-Trichlorobenzoyl chloride

Product 1

HCID 21509368N,N-Di(butan-2-yl)-2,3,5-trichlorobenzamide

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8471TriethylamineSolvent

Procedure

Into a 250 ml flask, provided with a reflux condenser, were introduced 10 g of 2,3,5-trichlorobenzoyl chloride in 20 ml of anhydrous C6H6, a solution of 5.3 g of di-sec.butylamine in 7 ml of anhydrous C6H6 and 5 g of triethylamine. This mass was then heated to reflux temperature for about 1 hour. Thereupon it was left to cool down to room temperature and the solvent was removed under reduced pressure in a rotating evaporator. The mass was then washed with acidulated H2O, with H2O and was then extracted with ethyl ether. The etheric extract was then dried on anhydrous Na2SO4, filtered and the solvent removed under reduced pressure. 12.6 g of yellowing crystals of 2,3,5-trichloro-N,N-di-sec.butyl-benzamide were obtained.

Workup

  1. customInto a 250 ml flask, provided with a reflux condenser
  2. temperatureThis mass was then heated
  3. temperatureto reflux temperature for about 1 hour
  4. waitThereupon it was left
  5. customthe solvent was removed under reduced pressure in a rotating evaporator
  6. washThe mass was then washed with acidulated H2O, with H2O
  7. extractionwas then extracted with ethyl ether
  8. extractionThe etheric extract
  9. dry with materialwas then dried on anhydrous Na2SO4
  10. filtrationfiltered
  11. customthe solvent removed under reduced pressure
  12. customwere obtained

Sources & evidence

ORD record
ord-2c7964a3b365418f96667e6950372401
Source dataset
uspto-grants-1976_09
Patent number
US03982931

Reaction notes

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