Hydrochloric Acid → HCID 54730047, compound

HRID 1579602Notes

Reaction equation

HRID 1579602 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[SH:10].[CH:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[C:13]([CH2:19]Cl)[CH:12]=1.Cl>N1C=CC=CC=1>[Cl:18][C:14]1[CH:15]=[C:16]([Cl:17])[CH:11]=[CH:12][C:13]=1[CH2:19][S:10][C:3]1[C:4](=[O:9])[O:5][C:6]([CH3:8])=[CH:7][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 72122,4-Dichlorobenzyl chlorideHCID 547312374-Hydroxy-3-mercapto-6-methyl-2-pyrone

Product 1

HCID 54730047HCID 54730047, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

4-Hydroxy-3-mercapto-6-methyl-2-pyrone (47.5 g., 0.300 mole) and α2,4-trichlorotoluene (58.6 g., 0.300 mole) were dissolved in pyridine (250 ml.). The temperature rose from 20° to 43°C. The solution was then heated at 90°C. for two hours, cooled and poured onto ice and 500 ml. of concd. hydrochloric acid. The resulting mixture was extracted with methylene chloride. The extract was dried (MgSO4) and the solvent removed by evaporation. The residue was mixed with hexane, filtered and dried, giving 53.3 g. (56 percent) of the desired product. Recrystallization from benzene gave the pure product as a white solid, m.p. 163°-164°C.

Workup

  1. customrose from 20° to 43°C
  2. temperaturecooled
  3. additionpoured onto ice and 500 ml
  4. extractionThe resulting mixture was extracted with methylene chloride
  5. dry with materialThe extract was dried (MgSO4)
  6. customthe solvent removed by evaporation
  7. additionThe residue was mixed with hexane
  8. filtrationfiltered
  9. customdried
  10. customgiving 53.3 g

Sources & evidence

ORD record
ord-6377d43b2ba44785a3263c922c94e846
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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