Thionyl Chloride → HCID 57706969, compound

HRID 1662479Notes

Reaction equation

HRID 1662479 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][C:11]=1[N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.S(Cl)([Cl:26])=O>CN(C=O)C.C(Cl)Cl>[Cl:26][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[C:11]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:12]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 57706049HCID 57706049, compound

Product 1

HCID 57706969HCID 57706969, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 67.20D (0.2318 g, 0.73 mmol) in dry DMF (0.03 mL) and dry DCM (3 mL) was added thionyl chloride (0.13 mL, 1.8 mmol) at 0° C. The resulting solution was warmed to room temperature and monitored with TLC and LCMS. After 45 minutes, the reaction was diluted with DCM and then washed once with saturated aqueous sodium bicarbonate and once with brine. After drying over anhydrous magnesium sulfate, filtering, and removing the solvent under reduced pressure, the residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford 67.20E (86.3 mg, 35% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.16 (1H, m), 7.00 (4H, m), 6.72 (1H, dt, J=9.0, 3.5 Hz), 4.50 (2H, s), 3.71 (3H, s), 2.71 (4H, m), 1.34 (6H, m).

Workup

  1. washwashed once with saturated aqueous sodium bicarbonate and once with brine
  2. dry with materialAfter drying over anhydrous magnesium sulfate
  3. filtrationfiltering
  4. customremoving the solvent under reduced pressure
  5. customthe residue was purified by silica gel flash chromatography (0-5% EtOAc/hexane)

Sources & evidence

ORD record
ord-aa55f5c8b78a4934ab5fe9cd66229249
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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