Water → HCID 66678607, compound

HRID 1528383Notes

Reaction equation

HRID 1528383 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH:8]2[CH2:10][CH2:9]2)[O:6][CH:7]=1.[K].[C:12]1(=[O:22])[NH:16][C:15](=[O:17])[C:14]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:13]12.O>CN(C=O)C>[CH:8]1([C:5]2[O:6][CH:7]=[C:3]([CH2:2][N:16]3[C:12](=[O:22])[C:13]4[C:14](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:15]3=[O:17])[N:4]=2)[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 6809PhthalimideHCID 5462222PotassiumHCID 580443194-(ChloroMethyl)-2-cyclopropyloxazole

Product 1

HCID 66678607HCID 66678607, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the stirred solution of 4-chloromethyl-2-cyclopropyl-oxazole (4.0 g, 25.38 mmol) in dry DMF (30 mL), was added potassium salt of phthalimide (4.7 g, 25.38 mmol) at rt. The resulting mixture was stirred for 24 h at rt and monitored through TLC. After completion of the reaction, water (200 mL) was added and the crude was extracted with ethyl acetate (3×50 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtained crude residue which was purified via column chromatography (100-200 silica gel, elution with 20% EtOAc in hexane). 3.5 g of 2-(2-cyclopropyl-oxazol-4-ylmethyl)-isoindole-1,3-dione was obtained as a white solid, 269.2 (M+H)+, which contained phthalimide. This compound was used for the next step as such.

Workup

  1. additionwas added
  2. extractionthe crude was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto obtained crude residue which
  7. customwas purified via column chromatography (100-200 silica gel, elution with 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-5f1a545ad5034dbba093819f174cf0c3
Source dataset
uspto-grants-2015_07
Patent number
US09090599B2

Reaction notes

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