HCID 15899924, compound → HCID 23458654, compound

HRID 1679938Notes

Reaction equation

HRID 1679938 reaction equation
Br[C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[S:16])[S-:15].C([NH+](CC)CC)C>C(#N)C>[CH3:5][C:2]1([CH3:6])[S:16][C:14](=[S:15])[N:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][N:7]=2)[CH:3]1[OH:4]

Participants

4

Reactant 2

HCID 15899924HCID 15899924, compoundHCID 234586692-bromo-2-methylpropan-1-ol

Product 1

HCID 23458654HCID 23458654, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
2 °C

Procedure

2-Bromo-2-methylpropanol (39.7 g) is added, at about 5° C., to a suspension of triethylammonium pyrid-2-yl-dithiocarbamate (71.2 g) in anhydrous acetonitrile (330 cc). The reaction is allowed to proceed for 1 hour at 20° C. The insoluble triethylamine hydrobromide is removed by filtration. The acetonitrile is evaporated off under reduced pressure (20 mm Hg) at 40° C. The residual oil is treated with methylene chloride (300 cc). The organic solution is washed twice with distilled water (100 cc in total), dried over sodium sulphate and evaporated. The resulting product (60 g) is dissolved in methylene chloride (300 cc), and the solution is filtered through silica (0.2-0.5 mm., 850 g) contained in a column of diameter 5 cm. Elution is carried out with methylene chloride (9 liters). After evaporating off the solvent under reduced pressure (20 mm Hg) at 40° C., the resulting product (50 g) is dissolved in boiling methylcyclohexane (150 cc). After cooling for 16 hours at 2° C., the crystals which have appeared are filtered off, washed with methylcyclohexane (50 cc) and dried under reduced pressure (0.1 mm Hg) at 40° C. 5,5-Dimethyl-4-hydroxy-3-(pyrid-2-yl)-thiazolidine-2-thione (44.1 g), which melts at 80° C., is thus obtained.

Workup

  1. customThe insoluble triethylamine hydrobromide is removed by filtration
  2. customThe acetonitrile is evaporated off under reduced pressure (20 mm Hg) at 40° C
  3. additionThe residual oil is treated with methylene chloride (300 cc)
  4. washThe organic solution is washed twice with distilled water (100 cc in total)
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. dissolutionThe resulting product (60 g) is dissolved in methylene chloride (300 cc)
  8. filtrationthe solution is filtered through silica (0.2-0.5 mm., 850 g)
  9. washElution
  10. customAfter evaporating off the solvent under reduced pressure (20 mm Hg) at 40° C.
  11. dissolutionthe resulting product (50 g) is dissolved
  12. filtrationthe crystals which have appeared are filtered off
  13. washwashed with methylcyclohexane (50 cc)
  14. customdried under reduced pressure (0.1 mm Hg) at 40° C

Sources & evidence

ORD record
ord-6d7a826d54ab45e58a65910fba8826fc
Source dataset
uspto-grants-1981_06
Patent number
US04271167

Reaction notes

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