Thionyl Chloride → 2-[4-(Chloromethyl)phenyl]-4-(pyrrolidin-1-ylcarbonyl)-1,3-oxazole

HRID 1716861Notes

Reaction equation

HRID 1716861 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[N:13]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:23])=O.N1C2C=CC=CC=2N=N1>C(Cl)Cl.C(Cl)(Cl)Cl>[Cl:23][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[N:13]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 57550216{4-[4-(Pyrrolidin-1-ylcarbonyl)-1,3-oxazol-2-yl]phenyl}methanolHCID 178418385HCID 178418385, compound

Product 1

HCID 575502282-[4-(Chloromethyl)phenyl]-4-(pyrrolidin-1-ylcarbonyl)-1,3-oxazoleYield 82%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-[4-(hydroxymethyl)phenyl]-4-(pyrrolidin-1-ylcarbonyl)-1,3-oxazole (0.467 g, 1.89 mmol) in CH2Cl2 was treated with a solution of thionyl chloride (0.281 g, 2.36 mmol) and benzotriazole (0.281 g, 2.36 mmol) in CH2Cl2, stirred for 6 hours at room temperature, diluted with CHCl3, filtered over Celite and concentrated under vacuum, The resultant residue was purified by flash chromatography (silica, MeOH:CH2Cl2 5%) to give the title product in 82% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 291 (MH+) mp 126-128° C.

Workup

  1. filtrationfiltered over Celite
  2. concentrationconcentrated under vacuum
  3. customThe resultant residue was purified by flash chromatography (silica, MeOH:CH2Cl2 5%)

Sources & evidence

ORD record
ord-a100cedd93574af891ce467520bcbf2d
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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