1-Bromo-3-chloropropane → HCID 20505173, compound

HRID 1701908Notes

Reaction equation

HRID 1701908 reaction equation
[OH-].[Na+].Cl.Cl.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][S:12][C:13](=N)N)[N:6]=1.BrC[CH2:18][CH2:19][Cl:20]>O>[Cl:20][CH2:19][CH2:18][CH2:13][S:12][CH2:11][C:7]1[N:6]=[N:5][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide2×HCID 20505182HCID 20505182, compound

Product 1

HCID 20505173HCID 20505173, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A 10 N aqueous solution of sodium hydroxide (84 cc) is added dropwise, in the course of 10 minutes and whilst keeping the temperature below 18° C., to a solution of 2-(pyridazin-3-ylmethyl)-isothiourea dihydrochloride (106 g) in distilled water (220 cc). After heating for 20 minutes at 75° C. and then cooling to 10° C., a 10 N aqueous solution of sodium hydroxide (50 cc) and then 1-bromo-3-chloropropane (69 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 (340 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 (80 g) contained in a column of diameter 2.7 cm; the column is then eluted with methylene chloride (700 cc). The first fraction (200 cc) is discarded. The second fraction (500 cc) is collected and concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 35° C. Pyridazin-3-ylmethyl 3-chloropropyl sulphide (60 g) is thus obtained in the form of a red oil.

Workup

  1. customthe temperature below 18° C.
  2. temperaturecooling to 10° C.
  3. stirringstirring
  4. extractionThe reaction mixture is then extracted three times with methylene chloride (340 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 (80 g)
  10. washthe column is then eluted with methylene chloride (700 cc)
  11. customThe second fraction (500 cc) is collected
  12. concentrationconcentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 35° C

Sources & evidence

ORD record
ord-f0f3aea125744e69a2f4dfbdb18ac5b7
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

Loading…