Thionyl Chloride → HCID 21976873, compound

HRID 19953Notes

Reaction equation

HRID 19953 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:16])[C:9]=1[S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[CH2:5]O.S(Cl)([Cl:19])=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:16])[C:9]=1[S:10](=[O:15])(=[O:14])[N:11]([CH3:13])[CH3:12])[CH2:5][Cl:19]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68562257HCID 68562257, compound

Product 1

HCID 21976873HCID 21976873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of OBS02015 (3.93 g, 10.10 mmol) in anhydrous-DCM (50 mL) was added thionyl chloride (1.11 mL, 15.15 mmol). The mixture was stirred at room temperature for 2 h and the volatiles removed in vacuo. The residue was re-dissolved and co-evaporated three times with DCM (3×20 mL) to give OBS02018 as a brown oil which solidified on standing (3.93 g, 96%). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.83; 1H-NMR (270 MHz, CDCl3)=3.11 (6H, s), 4.46 (2H, s) 7.59 (2H, s).

Workup

  1. customthe volatiles removed in vacuo
  2. dissolutionThe residue was re-dissolved

Sources & evidence

ORD record
ord-6b3e7d408d5143c79087916eebb69b1e
Source dataset
uspto-grants-2010_06
Patent number
US07745472B2

Reaction notes

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