Chloroform → HCID 56625968, compound

HRID 2118726Notes

Reaction equation

HRID 2118726 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][CH2:8][CH:9]([O:17][CH:18]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=1)[CH2:19][CH2:20]CO)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=1.[CH:30]([Cl:33])(Cl)Cl>O>[Cl:3][CH2:6][CH2:7][CH2:8][CH:9]([O:17][CH:18]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[N:24]=1)[CH2:19][CH2:20][CH2:30][Cl:33])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[N:11]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24386Thionyl ChlorideHCID 56612060HCID 56612060, compound

Product 1

HCID 56625968HCID 56625968, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of sulphinyl chloride (260 g) in chloroform (450 cc) maintained at a temperature below 10° C., 3-hydroxypropyl(6-methyl-2-pyridyl)methyl ether (339 g) is added in the course of 30 minutes. The mixture is then heated gradually and then maintained boiling for 1 hour. After being cooled to about 20° C., the mixture is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 50° C. The product obtained is dissolved in distilled water (1,000 cc) and the solution obtained is washed 3 times with diethyl ether (1,035 cc in total), filtered and then neutralised in the presence of diethyl ether (670 cc) with sodium bicarbonate (160 g). The decanted aqueous phase is saturated with sodium chloride and then extracted 3 times with diethyl ether (600 cc in total). The extracts are combined, dried over anhydrous magnesium sulphate in the presence of decolorising charcoal (17 g) and filtered. The filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa). 3-Chloropropyl(6-methyl-2-pyridyl)methyl ether (359.4 g) is thereby obtained in the from of a brown oil, and this is used as it is in the subsequent syntheses.

Workup

  1. additionis added in the course of 30 minutes
  2. temperatureThe mixture is then heated gradually
  3. temperaturemaintained
  4. concentrationthe mixture is concentrated under reduced pressure (30 mm Hg; 4 kPa) at 50° C
  5. customThe product obtained
  6. customthe solution obtained
  7. washis washed 3 times with diethyl ether (1,035 cc in total)
  8. filtrationfiltered
  9. extractionextracted 3 times with diethyl ether (600 cc in total)
  10. dry with materialdried over anhydrous magnesium sulphate in the presence of decolorising charcoal (17 g)
  11. filtrationfiltered
  12. concentrationThe filtrate is concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-b998dda84e3e43c6a884a5228da3e71f
Source dataset
uspto-grants-1987_07
Patent number
US04680303

Reaction notes

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