Diethyl Ether → HCID 23114632, compound

HRID 2080380Notes

Reaction equation

HRID 2080380 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([CH:11]([C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])O)=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)C>S(Cl)(Cl)=O.CN(C)C=O>[CH2:1]([O:4][C:5]1[C:6]([CH:11]([S:28][C:25]2[CH:26]=[CH:27][C:22]([Cl:21])=[CH:23][CH:24]=2)[C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=2[F:20])=[N:7][CH:8]=[CH:9][CH:10]=1)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 23114695HCID 23114695, compound

Product 1

HCID 23114632HCID 23114632, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 24386Thionyl ChlorideSolvent

Procedure

The 3-allyloxy-2-[(2,5-difluorophenyl)-hydroxymethyl]pyridine (370 mg, 1.33 mmol) obtained in Referential Example 10 was dissolved in thionyl chloride (2.0 ml). To the resulting solution was added a catalytic amount of dimethylformamide. The resulting mixture was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure. Dioxane was added to the residue, followed by further concentration. The residue thus obtained was dissolved in dimethylformamide (10 ml). To the resulting solution were added 4-chlorobenzenethiol (217 mg, 1.5 mmol) and potassium carbonate (828 mg, 6.0 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at 50° C. for 1 hour. After the reaction mixture was cooled to room temperature, diethyl ether (50 ml) was added thereto. The resulting mixture was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (hexane:ethyl acetate=10:1) to give the title compound (256 mg, 68%) as an oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionDioxane was added to the residue
  3. concentrationfollowed by further concentration
  4. customThe residue thus obtained
  5. stirringThe resulting mixture was stirred at 50° C. for 1 hour
  6. washThe resulting mixture was washed with water and brine
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3ee913565cee4459a88bd9aab6051709
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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