Hydrochloric Acid → HCID 178490206, compound

HRID 2188726Notes

Reaction equation

HRID 2188726 reaction equation
[OH-:1].[Na+].[CH2:3]([SH:7])[C:4](O)=O.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19].Cl>CO>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][CH2:4][C:3]([OH:1])=[S:7])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 14798Sodium HydroxideHCID 807854-(Chloromethyl)-2-nitroanisole

Product 1

HCID 178490206HCID 178490206, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold solution of sodium hydroxide (9.75 g, 240 mmol) in methanol (200 mL), thioglycollic acid (11.25 g, 120 mmol) was added slowly over 30 minutes. Sodium thioglycollate precipitated was dissolved by stirring and warming up the solution. The solution was cooled to room temperature and 4-methoxy-3-nitrobenzyl chloride (30.0 g, 120 mmol) was added in portions to reduce the intensity of exothermic reaction. The reaction mixture was then refluxed for 4 hours, cooled and poured onto crushed ice (1 Kg) containing hydrochloric acid (50 mL). The precipitate formed was filtered, washed with ice cold water and dried under vacuum. (30.0 g, 95% yield) m.p. 130-132° C.

Workup

  1. customSodium thioglycollate precipitated
  2. dissolutionwas dissolved
  3. temperaturewarming up the solution
  4. customthe intensity of exothermic reaction
  5. temperatureThe reaction mixture was then refluxed for 4 hours
  6. temperaturecooled
  7. additionpoured
  8. customThe precipitate formed
  9. filtrationwas filtered
  10. washwashed with ice cold water
  11. customdried under vacuum

Sources & evidence

ORD record
ord-daef8d6352984c808ad7756fd6f77bf5
Source dataset
uspto-grants-2012_12
Patent number
US08324190B2

Reaction notes

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