Thionyl Chloride → HCID 68663368, compound

HRID 452787Notes

Reaction equation

HRID 452787 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=4)[C:11]=3[CH:23]=2)=[N:4][N:3]=1.S(Cl)([Cl:26])=O>ClCCCl>[Cl:26][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:12]2[C:11]3[CH:23]=[C:7]([C:5]4[O:6][C:2]([CH3:1])=[N:3][N:4]=4)[CH:8]=[CH:9][C:10]=3[O:14][CH:13]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68664421HCID 68664421, compound

Product 1

HCID 68663368HCID 68663368, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of [4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]phenyl]methanol (204 mg, 0.66 mmol) in 1,2-dichloroethane (5 mL) was added thionyl chloride (0.240 mL, 3.33 mmol), and the resulting mixture was heated under reflux for 1 hr. After cooling, the reaction mixture was concentrated under reduced pressure to give crude 2-[3-[4-(chloromethyl)phenyl]-1-benzofuran-5-yl]-5-methyl-1,3,4-oxadiazole as yellow crystals.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc889ca4f1f1489e99dbb3d0c1c2a867
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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