Chlorosuccinimide → HCID 89995598, compound

HRID 1480846Notes

Reaction equation

HRID 1480846 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 cooling to room temperature and partitioning 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 residue was absorbed on silica gel (1.4 g) and purified using silica gel column chromatography eluting with 0-30% EtOAc in DCM to afford the title compound (0.130 g, 49%).

Workup

  1. temperaturebefore cooling to room temperature
  2. custompartitioning 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 residue was absorbed on silica gel (1.4 g)
  7. custompurified
  8. washeluting with 0-30% EtOAc in DCM

Sources & evidence

ORD record
ord-313558d6d9ac44ba83eb9aaf17d3f5c3
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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