Chlorosuccinimide → HCID 89995598, compound

HRID 523083Notes

Reaction equation

HRID 523083 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)=[N:4][N:3]=1.[Cl:14]N1C(=O)CCC1=O>CN(C=O)C>[Cl:14][C:12]1[CH:13]=[C:7]([C:5]2[O:6][C:2]([CH3:1])=[N:3][N:4]=2)[CH:8]=[CH:9][C:10]=1[NH2:11]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 195422444-(5-Methyl-1,3,4-oxadiazol-2-yl)aniline

Product 1

HCID 89995598HCID 89995598, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 4-(5-methyl-1,3,4-oxadiazol-2-yl)aniline (0.220 g, 1.26 mmol) and anhydrous DMF (1.9 mL) was added N-chlorosuccinimide (0.168 g, 1.26 mmol). The reaction mixture was heated at 40° C. for 1.5 hours under argon before being allowed to cool to room temperature and partitioned between EtOAc (90 mL) and saturated aqueous NaHCO3 (15 mL). The organic layer was washed with saturated aqueous NaHCO3 (15 mL), dried (Na2SO4) and concentrated in vacuo. The brown residue was absorbed on silica gel (1.4 g), and purified using silica gel column chromatography eluting with a gradient of 0-30% EtOAc in CH2Cl2 to afford the title compound as a white solid (0.130 g, 49%).

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc (90 mL) and saturated aqueous NaHCO3 (15 mL)
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (15 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe brown residue was absorbed on silica gel (1.4 g)
  7. custompurified
  8. washeluting with a gradient of 0-30% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-5abd0becd9814b9a9a26fe478d3e29ae
Source dataset
uspto-grants-2016_05
Patent number
US09334286B2

Reaction notes

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