Hydrochloric Acid → HCID 13151845, compound

HRID 485409Notes

Reaction equation

HRID 485409 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[C:9]([OH:18])(=[O:17])[C:10]1[C:11](=[CH:13][CH:14]=[CH:15][CH:16]=1)[SH:12].N1C2C(=CC=CC=2)C=CC=1.Cl>N1C=CC=CC=1>[Br:8][C:4]1[CH:3]=[C:2]([S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]([OH:18])=[O:17])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 54432-Mercaptobenzoic AcidHCID 7047QuinolineHCID 79271,3-Dibromobenzene

Product 1

HCID 13151845HCID 13151845, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture consisting of 179 g. m-dibromobenzene (0.758 mole); 46.6 g. thiosalicyclic acid (0.303 mole); 25.9 g cuprous oxide (0.181 mole); 212 cc. quinoline; and 24 cc. pyridine is mechanically stirred and heated in an oil bath at 200° C. to 210° C. for three hours. The internal temperature remains constant at 145° C. The reaction mixture is then poured into 1500 cc. of 5N aqueous HCl. The oily solid is filtered, then dissolved in 750 cc. 1N aqueous NaOH solution; this solution is filtered through celite, then extracted three times with ether. The aqueous fraction is acidified with concentrated HCl and the resulting grayish solid filtered, washed well with water and dried. The crude yield obtained is 65 g. (69.4%). It is used as such in the next step.

Workup

  1. temperatureheated in an oil bath at 200° C. to 210° C. for three hours
  2. customremains constant at 145° C
  3. additionThe reaction mixture is then poured into 1500 cc
  4. filtrationThe oily solid is filtered
  5. dissolutiondissolved in 750 cc
  6. filtrationthis solution is filtered through celite
  7. extractionextracted three times with ether
  8. filtrationthe resulting grayish solid filtered
  9. washwashed well with water
  10. customdried
  11. customThe crude yield
  12. customobtained

Sources & evidence

ORD record
ord-b01ca5702dc34bb2a08ef513f4716e29
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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