Thionyl Chloride → HCID 57707149, compound

HRID 1662436Notes

Reaction equation

HRID 1662436 reaction equation
[O:1]1[CH2:6][CH:5]=[C:4]([C:7]2[CH:12]=[C:11]([CH2:13]O)[CH:10]=[CH:9][C:8]=2[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])[CH2:3][CH2:2]1.S(Cl)([Cl:26])=O>C(Cl)Cl.CN(C=O)C>[Cl:26][CH2:13][C:11]1[CH:10]=[CH:9][C:8]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])=[C:7]([C:4]2[CH2:3][CH2:2][O:1][CH2:6][CH:5]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 57706234HCID 57706234, compound

Product 1

HCID 57707149HCID 57707149, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 66.46G (39.3 mg, 0.13 mmol) in dry DCM (1.0 mL) and dry DMF (0.010 mL) was added thionyl chloride (0.020 mL, 0.27 mmol) at 0° C. The resulting solution was warmed to room temperature and monitored with TLC and LCMS. After 45 minutes, the reaction was concentrated and then purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford 66.46H (39.5 mg, 95% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.39 (3H, m), 7.02 (1H, t, J=8.8 Hz), 6.85 (2H, m), 5.57 (1H, s), 4.64 (2H, s), 4.13 (2H, q, J=2.7 Hz), 3.80 (3H, s), 3.70 (2H, t, J=5.3 Hz), 2.14 (2H, dd, J=4.5, 2.5 Hz).

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by silica gel flash chromatography (0-5% EtOAc/hexane)

Sources & evidence

ORD record
ord-7bfe85d6e71b41c89a6d238ff9376f82
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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