1-Bromo-3-chloropropane → HCID 20505184, compound

HRID 1701886Notes

Reaction equation

HRID 1701886 reaction equation
[OH-].[Na+].Cl.Cl.[N:5]1[CH:10]=[CH:9][C:8]([CH2:11][S:12][C:13](=N)N)=[CH:7][CH:6]=1.BrC[CH2:18][CH2:19][Cl:20]>O>[Cl:20][CH2:19][CH2:18][CH2:13][S:12][CH2:11][C:8]1[CH:9]=[CH:10][N:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide2×HCID 13043949HCID 13043949, compound

Product 1

HCID 20505184HCID 20505184, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
83 °C

Procedure

A 10 N aqueous solution of sodium hydroxide (97 cc) is added dropwise, in the course of 15 minutes and whilst keeping the temperature below 14° C., to a solution of 2-(pyrid-4-yl-methyl)-isothiourea dihydrochloride (116.5 g) in distilled water (240 cc). After heating for 20 minutes at 83° C. and then cooling to 12° C., a 10 N aqueous solution of sodium hydroxide (60 cc) and then 1-bromo-3-chloropropane (81.5 g) are added, whilst stirring, and stirring is continued for 15 hours at a temperature of about 20° C. The reaction mixture is then extracted three times with methylene chloride (430 cc in total); the organic extracts are combined, washed with distilled water (250 cc) and dried over anhydrous sodium sulphate. After filtration, the solution obtained is poured onto neutral silica gel (125 g) contained in a column of diameter 3.2 cm; the column is then eluted with methylene chloride (1600 cc). The first fraction (400 cc) is discarded; the second fraction (1200 cc) is collected and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. Pyrid-4-yl-methyl 3-chloropropyl sulphide (81 g) is thus obtained in the form of a brown oil.

Workup

  1. customthe temperature below 14° C.
  2. temperaturecooling to 12° C.
  3. stirringstirring
  4. extractionThe reaction mixture is then extracted three times with methylene chloride (430 cc in total)
  5. washwashed with distilled water (250 cc)
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationAfter filtration
  8. customthe solution obtained
  9. additionis poured onto neutral silica gel (125 g)
  10. washthe column is then eluted with methylene chloride (1600 cc)
  11. customthe second fraction (1200 cc) is collected
  12. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-4bed8cc46e9b4a93916c9cceac1a5efc
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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