Thionyl Chloride → HCID 86054120, compound

HRID 1010539Notes

Reaction equation

HRID 1010539 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH:13](O)[CH3:14])[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH2:13][CH2:14][Cl:18])[CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86652005HCID 86652005, compound

Product 1

HCID 86054120HCID 86054120, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred solution of 1.0 gram (0.0044 mole) of 2 {[(6-chloro(3-pyridyl))methyl]propylamino}ethan-1-ol in two mL of chloroform was cooled to 0° C., and 2 mL (excess) of thionyl chloride was added dropwise. Upon completion of addition the reaction mixture was allowed to warm to ambient temperature, and then it was heated to reflux where it was stirred for one hour. After this time the reaction mixture was concentrated and made basic with aqueous 10% sodium hydroxide. The mixture was then extracted multiple times with ethyl acetate. The combined extracts were then dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding about 1.0 gram of the subject compound.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. temperatureit was heated
  3. temperatureto reflux where it
  4. concentrationAfter this time the reaction mixture was concentrated
  5. extractionThe mixture was then extracted multiple times with ethyl acetate
  6. dry with materialThe combined extracts were then dried with magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f84168d4319546e5a076636f217384bc
Source dataset
uspto-grants-2011_07
Patent number
US07977332B2

Reaction notes

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