1-Bromo-3-chloropropane → Quinol-3-ylmethyl 3-chloropropyl sulphide

HRID 1701913Notes

Reaction equation

HRID 1701913 reaction equation
[OH-].[Na+].Cl.Cl.[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([CH2:15][S:16][C:17](=N)N)[CH:6]=1.BrC[CH2:22][CH2:23][Cl:24]>O>[Cl:24][CH2:23][CH2:22][CH2:17][S:16][CH2:15][C:7]1[CH:6]=[N:5][C:14]2[C:9]([CH:8]=1)=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium Hydroxide2×HCID 201355072-(Quinol-3-ylmethyl)-isothiourea dihydrochloride

Product 1

HCID 20505176Quinol-3-ylmethyl 3-chloropropyl sulphideYield 17.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A 10 N aqueous solution of sodium hydroxide (40.8 cc) is added in the course of 9 minutes, and whilst allowing the temperature to rise to 10° C., to a solution, cooled to 1° C., of 2-(quinol-3-ylmethyl)-isothiourea dihydrochloride (59.2 g) in distilled water (100 cc). After heating for 20 minutes at a temperature of about 70° C. and then cooling to 12° C., a 10 N aqueous solution of sodium hydroxide (25 cc) is added dropwise in the course of 5 minutes. 1-Bromo-3-chloropropane (33.6 g) is then added and stirring is continued for 20 hours at a temperature of about 20° C. The reaction mixture is then extracted three times with methylene chloride (400 cc in total). The organic extracts are combined, washed with distilled water (100 cc), dried over anhydrous sodium sulphate and concentrated under reduced pressure (20 mm Hg; 2.7 kPa) at 35° C. so as to bring the volume to about 100 cc. The solution thus obtained is chromatographed on neutral silica gel (250 g) contained in a column of diameter 3.8 cm. Elution is carried out with methylene chloride (1500 cc), one 600 cc fraction and one 900 cc fraction being collected. The latter fraction is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 35° C. Quinol-3-ylmethyl 3-chloropropyl sulphide (9.2 g) is thus obtained in the form of a yellow oil.

Workup

  1. customto rise to 10° C., to a solution
  2. temperaturecooling to 12° C.
  3. extractionThe reaction mixture is then extracted three times with methylene chloride (400 cc in total)
  4. washwashed with distilled water (100 cc)
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure (20 mm Hg; 2.7 kPa) at 35° C. so as
  7. customThe solution thus obtained
  8. customis chromatographed on neutral silica gel (250 g)
  9. washElution
  10. custombeing collected
  11. concentrationThe latter fraction is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 35° C

Sources & evidence

ORD record
ord-ef395594c56740f19885e156e192f92a
Source dataset
uspto-grants-1983_04
Patent number
US04379154

Reaction notes

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