Aniline → HCID 10703669, compound

HRID 1288485Notes

Reaction equation

HRID 1288485 reaction equation
[CH:1]1([NH:7][C:8]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:17]C1C=CC=CC=1>O1CCCC1>[C:1]1([N:7]=[C:8]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)[NH2:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 236099N-cyclohexyl-3-methylbenzamide

Product 1

HCID 10703669HCID 10703669, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

65.1 g (0.3 mole) of N-cyclohexyl-m-toluamide were dissolved in 500 ml of dried tetrahydrofuran and a benzene solution of 45 g of COCl2 absorbed in 30 ml dried benzene, and 30 ml dried pyridine were added dropwise and under agitation and ice cooling to the above tetrahydrofuran solution. Upon completion of the dropwise addition, the reaction mixture was adjusted in its temperature to room temperature and brought into reaction for 2 hours. The sedimented pyridine hydrochloride were filtered off and the filtrate was condensed under vacuo, to provide an oily substance containing N-cyclohexyl-m-toluimido chloride. The oil was then subjected to extraction with 400 ml of dried petroleum ether and 32.8 ml (0.36 mole) of aniline were added dropwise for 30 minutes under agitation and ice cooling to the extract and the mixture was let to react at room temperature for 1.5 hours. The thus deposited oily substance was decanted off from the mother liquor and dissolved in 100 ml of ethanol, adjusted pH to about 2 by addition of 1N-hydrochloric acid and added with 1.2 lit. of water. Then, the aqueous solution was washed twice with 150 ml of ethyl acetate. The aqueous phase was treated with active carbon for discoloration and then condensed under vacuo. The sedimented products were filtered off, washed, dried and recrystallized from ethanol/diethyl ether. In this way, 81.7 g of N-cyclohexyl, N'-phenyl-m-toluamidine were obtained. m.p. 174° - 176° C. Yield: 82.9%.

Workup

  1. customa benzene solution of 45 g of COCl2 absorbed in 30 ml dried benzene
  2. addition30 ml dried pyridine were added dropwise and under agitation and ice cooling to the above tetrahydrofuran solution
  3. additionUpon completion of the dropwise addition
  4. customwas adjusted in its temperature to room temperature
  5. custombrought into reaction for 2 hours
  6. filtrationThe sedimented pyridine hydrochloride were filtered off
  7. customcondensed under vacuo
  8. customto provide an oily substance
  9. additionwere added dropwise for 30 minutes under agitation and ice cooling to the
  10. extractionextract
  11. customto react at room temperature for 1.5 hours
  12. customThe thus deposited oily substance was decanted off from the mother liquor
  13. dissolutiondissolved in 100 ml of ethanol
  14. additionadjusted pH to about 2 by addition of 1N-hydrochloric acid
  15. additionadded with 1.2 lit. of water
  16. washThen, the aqueous solution was washed twice with 150 ml of ethyl acetate
  17. additionThe aqueous phase was treated with active carbon for discoloration
  18. customcondensed under vacuo
  19. filtrationThe sedimented products were filtered off
  20. washwashed
  21. customdried
  22. customrecrystallized from ethanol/diethyl ether

Sources & evidence

ORD record
ord-aadc59f27db548aab33c93535f5e2807
Source dataset
uspto-grants-1976_10
Patent number
US03988364

Reaction notes

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