Triethylamine → HCID 20084545, compound

HRID 1609272Notes

Reaction equation

HRID 1609272 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=1[C:11]([O:13]CC)=[O:12].C(N(CC)CC)C.[CH2:27]([O:34][C:35]1[CH:43]=[CH:42][C:38]([C:39](Cl)=[O:40])=[CH:37][CH:36]=1)/[CH:28]=[CH:29]/[CH2:30][CH2:31][CH2:32][CH3:33]>C(Cl)Cl>[CH2:27]([O:34][C:35]1[CH:36]=[CH:37][C:38]([C:39]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([OH:13])=[O:12])=[O:40])=[CH:42][CH:43]=1)/[CH:28]=[CH:29]/[CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20084430HCID 20084430, compoundHCID 20084463HCID 20084463, compound

Product 1

HCID 20084545HCID 20084545, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 30 ml of methylene chloride were dissolved 2.1 g of ethyl 2-(2-aminophenylthio)benzoate and 1.8 g of triethylamine, followed by dropwise addition of 2.2 g of (E)-4-(2-heptenyloxy)benzoyl chloride with ice-cooling and stirring. The mixture was stirred at room temperature for 10 hours, and then the methylene chloride was distilled off. The residue was diluted with water and extracted with ether. The ether layer was washed with diluted hydrochloric acid and saturated sodium hydrogen carbonate solution and dried and the ether was distilled off. The oily residue was dissolved in 50 ml of ethanol followed by addition of 7 ml of 10% aqueous sodium hydroxide solution, and the mixture was heated on a water bath for 40 minutes. After cooling, the reaction mixture was acidified with hydrochloric acid and diluted with water and the crystals separated out therefrom were collected by filtration and washed with water and aqueous ethanol in that order to give 2.8 g of the title compound as white crystals.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 10 hours
  3. distillationthe methylene chloride was distilled off
  4. additionThe residue was diluted with water
  5. extractionextracted with ether
  6. washThe ether layer was washed with diluted hydrochloric acid and saturated sodium hydrogen carbonate solution
  7. customdried
  8. distillationthe ether was distilled off
  9. dissolutionThe oily residue was dissolved in 50 ml of ethanol
  10. additionfollowed by addition of 7 ml of 10% aqueous sodium hydroxide solution
  11. temperaturethe mixture was heated on a water bath for 40 minutes
  12. temperatureAfter cooling
  13. additiondiluted with water
  14. customthe crystals separated out
  15. filtrationtherefrom were collected by filtration
  16. washwashed with water and aqueous ethanol in that order

Sources & evidence

ORD record
ord-37329cc095a84da0b7a5e71da50e75fb
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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