Thionyl Chloride → HCID 57706691, compound

HRID 1662448Notes

Reaction equation

HRID 1662448 reaction equation
[CH3:1][C:2]1([CH3:26])[C:6]([C:7]2[CH:12]=[C:11]([CH2:13]O)[CH:10]=[CH:9][C:8]=2[C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=2[F:25])=[CH:5][CH2:4][CH2:3]1.S(Cl)([Cl:29])=O>C(Cl)Cl.CN(C=O)C>[Cl:29][CH2:13][C:11]1[CH:10]=[CH:9][C:8]([C:15]2[CH:20]=[C:19]([C:21]([F:23])([F:22])[F:24])[CH:18]=[CH:17][C:16]=2[F:25])=[C:7]([C:6]2[C:2]([CH3:26])([CH3:1])[CH2:3][CH2:4][CH:5]=2)[CH:12]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 57706041HCID 57706041, compound

Product 1

HCID 57706691HCID 57706691, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 66.53B (0.2574 g, 0.706 mmol) in dry DCM (10 mL) and dry DMF (0.07 mL) was added thionyl chloride (0.11 mL, 1.51 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 66.53C (242.8 mg, 90% yield). 1H NMR (400 MHz, CDCl3) 6 ppm 7.60 (2H, m), 7.40 (1H, m), 7.35 (2H, m), 7.21 (1H, m), 5.52 (1H, td, J=2.4, 0.9 Hz), 4.66 (2H, m), 2.24 (2H, td, J=7.0, 2.3 Hz), 1.68 (2H, m), 0.84 (6H, s).

Workup

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

Sources & evidence

ORD record
ord-823d43bae41c424681b6d8e9ce5856e4
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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