Ethanol → HCID 18516105, compound

HRID 1508223Notes

Reaction equation

HRID 1508223 reaction equation
[Cl:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16][CH2:17]O>C(Cl)Cl.CN(C=O)C>[CH2:16]([O:5][C:4](=[O:6])[C:3]1[C:2]([Cl:1])=[CH:10][N:9]=[CH:8][C:7]=1[Cl:11])[CH3:17]

Participants

6

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 6057633,5-Dichloroisonicotinic acid

Product 1

HCID 18516105HCID 18516105, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 3,5-dichloroisonicotinic acid (52 mmol) in 250 mL DCM and 5 mL DMF were added 11.4 mL thionylchloride. The mixture was heated to 40° C. for 2.5 h, cooled to RT before 100 mL EtOH were added. The solution was stirred at RT for 10 min and then concentrated in vacuo. The crude mixture was taken up in EtOAc and quenched with sat. aq. NaHCO3 solution under ice cooling. The aqueous layer was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by CC using Hept/EtOAc (95/5 to 85/15) gives the desired product as colorless oil;

Workup

  1. additionwere added
  2. concentrationconcentrated in vacuo
  3. customquenched with sat. aq. NaHCO3 solution under ice cooling
  4. extractionThe aqueous layer was extracted with EtOAc (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by CC

Sources & evidence

ORD record
ord-f834014a5cfb4c82956840dea83382a5
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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