Hydrochloric Acid → HCID 135736893, compound

HRID 1757216Notes

Reaction equation

HRID 1757216 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1.[CH2:11]1[C:16](=[O:17])[S:15][CH2:14][C:12]1=[O:13].[OH-].[K+].Cl>O1CCOCC1.O>[OH:13][C:12]1[CH2:14][S:15][C:16](=[O:17])[C:11]=1[CH2:7][C:6]1[CH:9]=[CH:10][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10214383Thiotetronic acidHCID 113679304-(Methylthio)benzyl bromide

Product 1

HCID 135736893HCID 135736893, compoundYield 26.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 4-methylthiobenzyl bromide (5.6 g. 25.8 mmol), thiotetronic acid (3.0 g, 25.8 mmol) in dioxane (50 ml), was added aqueous potassium hydroxide (25.8 mL). The mixture was stirred at temperatures in the range of 65°-70° C. for 3 hours. Then, the mixture was cooled to room temperature, poured into H2O, acidified with HCl (2N) and extracted with EtOAc. The organic extracts were dried over MgSO4. Evaporation and purification by flash chromatography on acid washed (5% H3PO4 in MeOH) silica gel (eluting solvent hexane/EtOAc 1/3) gave a white solid (1.72 g, 26.5%): m.p. 206°-208° C.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic extracts were dried over MgSO4
  3. customEvaporation and purification by flash chromatography on acid
  4. washwashed (5% H3PO4 in MeOH) silica gel (eluting solvent hexane/EtOAc 1/3)

Sources & evidence

ORD record
ord-1ddff3fd1a5b4a6684a52f905c20f779
Source dataset
uspto-grants-1995_08
Patent number
US05444086

Reaction notes

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