1-Bromo-3-chloropropane → HCID 12893092, compound

HRID 1680187Notes

Reaction equation

HRID 1680187 reaction equation
[OH-].[Na+].Cl.Cl.[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][S:12][C:13](=N)N.BrC[CH2:18][CH2:19][Cl:20]>O>[Cl:20][CH2:19][CH2:18][CH2:13][S:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][N:5]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide2×HCID 130439522-(2-Pyridiniomethyl)isothiouronium dichloride

Product 1

HCID 12893092HCID 12893092, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
70 °C

Procedure

A solution of sodium hydroxide pellets (151 g) in distilled water (342 cc) is added, in the course of 5 minutes, at a temperature which does not exceed 10° C., to a solution, originally at 5° C., of 2-(pyrid-2-ylmethyl)-isothiourea dihydrochloride (453 g) in distilled water (840 cc). After heating the reaction mixture for 20 minutes at a temperature of about 70° C., and then cooling to 3° C., a solution of sodium hydroxide pellets (92.5 g) in distilled water (210 cc) is added dropwise in the course of 3 minutes. After stirring the reaction mixture for 5 minutes at 10° C., 1-bromo-3-chloropropane (303 g) is added. Stirring is then continued for 20 hours at a temperature of about 20° C. The reaction mixture is then extracted four times with methylene chloride (1100 cc in total). The combined organic extracts are washed three times with distilled water (600 cc in total) and then dried over anhydrous sodium sulphate. After filtering, the resulting solution is poured onto neutral silica gel (380 g) contained in a column of diameter 6 cm, and the column is then washed with methylene chloride (2700 cc). A first fraction of effluent (600 cc) is discarded and a second fraction (3200 cc) is then collected and concentrated to dryness under reduced pressure (20 mm Hg) at 20° C. Pyrid-2-ylmethyl 3-chloropropyl sulphide (330 g) is thus obtained in the form of a yellow liquid.

Workup

  1. temperaturecooling to 3° C.
  2. stirringStirring
  3. waitis then continued for 20 hours at a temperature of about 20° C
  4. extractionThe reaction mixture is then extracted four times with methylene chloride (1100 cc in total)
  5. washThe combined organic extracts are washed three times with distilled water (600 cc in total)
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationAfter filtering
  8. additionthe resulting solution is poured onto neutral silica gel (380 g)
  9. washthe column is then washed with methylene chloride (2700 cc)
  10. customa second fraction (3200 cc) is then collected
  11. concentrationconcentrated to dryness under reduced pressure (20 mm Hg) at 20° C

Sources & evidence

ORD record
ord-b2740915a412430ea634680c8bb2876d
Source dataset
uspto-grants-1981_06
Patent number
US04272534

Reaction notes

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