Pyridine → HCID 20084520, compound

HRID 1609280Notes

Reaction equation

HRID 1609280 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=1[C:11]#[N:12].N1C=CC=CC=1.C([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)(=O)C>CCOCC>[C:11]([C:10]1[CH:13]=[CH:14][CH:15]=[CH:16][C:9]=1[S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:31](=[O:32])[C:30]1[CH:34]=[CH:35][C:27]([OH:26])=[CH:28][CH:29]=1)#[N:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3662332-(2-Aminophenyl)sulfanylbenzonitrileHCID 2756254p-Acetoxybenzoyl chloride

Product 1

HCID 20084520HCID 20084520, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

In 60 ml of ether were dissolved 2.6 g of 2-(2-aminophenylthio)benzonitrile (prepared in accordance with Reference Example 5, Step 4) and 2.8 g of pyridine, followed by dropwise addition of a solution of 2.7 g of 4-acetoxybenzoyl chloride in ether with ice-cooling and stirring. After completion of dropwise addition, the mixture was stirred at room temperature for 10 hours. The ether was then distilled off and ethanol was added to the residue. The resulting crystals were collected by filtration and washed with ethanol. The crystals were then suspended in 70 ml of ethanol, and after 7 ml of 10% aqueous sodium hydroxide solution was added, the mixture was stirred at room temperature for 1 hour. The reaction mixture was acidified with concentrated hydrochloric acid and diluted with water. The crystals separated out therefrom were collected by filtration and dried to give 3.3 g of the title compound as white crystals.

Workup

  1. temperaturecooling
  2. additionAfter completion of dropwise addition
  3. stirringthe mixture was stirred at room temperature for 10 hours
  4. distillationThe ether was then distilled off
  5. additionethanol was added to the residue
  6. filtrationThe resulting crystals were collected by filtration
  7. washwashed with ethanol
  8. additionafter 7 ml of 10% aqueous sodium hydroxide solution was added
  9. stirringthe mixture was stirred at room temperature for 1 hour
  10. additiondiluted with water
  11. customThe crystals separated out
  12. filtrationtherefrom were collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-1369ea0d37854cc3a45b341d2921cec0
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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