Thionyl Chloride → HCID 22158041, compound

HRID 1073171Notes

Reaction equation

HRID 1073171 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:11]=[CH:10][C:9](/[C:12](/[C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[CH:13]\[CH2:14][CH2:15][CH2:16]O)=[CH:8][CH:7]=1>>[ClH:3].[Cl:3][CH2:16][CH2:15][CH2:14]/[CH:13]=[C:12](/[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)\[C:9]1[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 15087804HCID 15087804, compound

Product 1

HCID 22158041HCID 22158041, compoundYield 94.4%

Procedure

160 parts of thionyl chloride were added dropwise to 10 parts of (E)-5-(4-fluorophenyl)-5-(3-pyridinyl)-4-penten-1-ol while stirring (exothermic reaction, the temperature rose to 45° C.). Upon complete addition, stirring was continued for 2 hours at room temperature. The reaction mixture was evaporated. The residue was taken up in methylbenzene and the solvent was evaporated again. The residue was solidified in 2,2'-oxybispropane. The product was filtered off and dried, yielding 11.5 parts (94.4%) of (E)-3-[5-chloro-1-(4-fluorophenyl)-1-pentenyl]pyridine hydrochloride (int. 60).

Workup

  1. customexothermic reaction
  2. customrose to 45° C.
  3. additionUpon complete addition
  4. stirringstirring
  5. customThe reaction mixture was evaporated
  6. customthe solvent was evaporated again
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-4d8616022cc149daa310c4fb6974c992
Source dataset
uspto-grants-1990_11
Patent number
US04968684

Reaction notes

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