Thionyl Chloride → HCID 21935942, compound

HRID 1242294Notes

Reaction equation

HRID 1242294 reaction equation
[CH3:1][C:2]1[C:7]([CH:8](O)[CH2:9][CH2:10][CH3:11])=[CH:6][CH:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:3]=1.O=S(Cl)[Cl:25]>C(Cl)Cl>[Cl:25][CH:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[CH:5][CH:6]=1)[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935690[Rac]-1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-ol

Product 1

HCID 21935942HCID 21935942, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.276 g (0.892 mmol) of the above prepared [rac]-1-[2-methyl-6-(3-trifluoromethyl-phenyl)-pyridin-3-yl]-butan-1-ol was dissolved in 4.3 ml of CH2Cl2 and treated dropwise at 0° C. with 0.13 ml (2 eq.) of SOCl2. The reaction mixture was kept at 0° C. for 5 Min. and at RT for 30 Min. Pouring onto crashed ice/NaHCO3, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents yielded 0.289 g of pure title compound as light yellow oil.

Workup

  1. customwas kept at 0° C. for 5 Min
  2. customat RT
  3. additionPouring
  4. extractionice/NaHCO3, twofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-dd4d75fdbc4d4d3c802009b299ff63a1
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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