Hydrochloric Acid → HCID 20205019, compound

HRID 978071Notes

Reaction equation

HRID 978071 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([SH:11])=[CH:4][CH:3]=1.Br[CH:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([OH:16])=[O:15].Cl>[OH-].[Na+]>[C:7]([C:6]1[CH:10]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[S:11][CH:13]([CH2:17][CH2:18][CH2:19][CH3:20])[C:14]([OH:16])=[O:15])([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 120132-Bromohexanoic acidHCID 155577875-Chloro-2-sulfanylbenzoic acid

Product 1

HCID 20205019HCID 20205019, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 5-chlorothiosalicylic acid [prepared by the process set forth in L. Katz et al., J. Org. Chem., 18 (1953) 1380] (2.0 g, 9.8 mmol) and 1N aqueous sodium hydroxide (100 ml) was heated at reflux temperature for 1 hour under a nitrogen atmosphere. 2-Bromohexanoic acid (1.9 g, 9.8 mmol) was then added, and refluxing was continued for an additional hour. The mixture was cooled in an ice bath and acidified with concentrated hydrochloric acid. The acidic mixture was extracted with diethyl ether, and the combined organic layers were washed with water, saturated aqueous sodium chloride solution, dried (sodium sulfate), and evaporated. The product was obtained as a light yellow solid (2.4 g) that was used without further purification in the subsequent step below.

Workup

  1. customprepared by the process
  2. temperatureat reflux temperature for 1 hour under a nitrogen atmosphere
  3. temperaturerefluxing
  4. waitwas continued for an additional hour
  5. temperatureThe mixture was cooled in an ice bath
  6. extractionThe acidic mixture was extracted with diethyl ether
  7. washthe combined organic layers were washed with water, saturated aqueous sodium chloride solution
  8. dry with materialdried (sodium sulfate)
  9. customevaporated

Sources & evidence

ORD record
ord-2f768ecc289b410a90e91d52c1483e33
Source dataset
uspto-grants-1987_05
Patent number
US04663344

Reaction notes

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