Dimethylformamide → HCID 178497721, compound

HRID 1488120Notes

Reaction equation

HRID 1488120 reaction equation
[C:1]([C:3]1[NH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:11]([O:13][CH3:14])=[O:12])=[CH:6][N:7]=1)#[N:2].CN(C=O)C.C1C(=O)N([Cl:31])C(=O)C1>C(Cl)(Cl)Cl>[Cl:31][C:6]1[N:7]=[C:3]([C:1]#[N:2])[NH:4][C:5]=1[C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][C:17]=1[CH3:18])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 90030834HCID 90030834, compound2×

Product 1

HCID 178497721HCID 178497721, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-(2-cyano-1H-imidazol-5-yl)-4-methylbenzoate (compound 234.3, 290 mg, 1.20 mmol) in a solvent mixture of DMF and CHCl3 (4/20 mL). NCS (161 mg, 1.21 mmol, 1.00 equiv) was added to the above reaction mixture. The reaction mixture was stirred overnight at room temperature, then was concentrated under reduced pressure. The residue was diluted with 30 mL of EtOAc, then was washed with 3×15 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/10-1/7) as eluent to furnish 160 mg (48%) of the title compound as light yellow oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationwas concentrated under reduced pressure
  3. additionThe residue was diluted with 30 mL of EtOAc
  4. washwas washed with 3×15 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/10-1/7) as eluent

Sources & evidence

ORD record
ord-0bb34e1fd3714802adf714c43e574839
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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