Chloroform → HCID 178497715, compound

HRID 1488132Notes

Reaction equation

HRID 1488132 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12]1[NH:16][C:15]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:14][CH:13]=1.C(Cl)(Cl)[Cl:24]>>[Cl:24][C:13]1[N:14]=[C:15]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[NH:16][C:12]=1[C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[CH3:1])[C:6]([O:8][CH3:9])=[O:7]

Participants

3

Reactant 2

HCID 6212ChloroformHCID 90029560HCID 90029560, compound2×

Product 1

HCID 178497715HCID 178497715, compound

Conditions

Temperature
25 °C

Procedure

Into a 25-mL round-bottom flask, was placed a solution of methyl 4-methyl-3-(2-(tetrahydro-2H-pyran-4-yl)-1H-imidazol-5-yl)benzoate (compound 241.2, 260 mg, 0.87 mmol) in chloroform (3 mL) NCS (116 mg, 0.87 mmol) was added to the reaction. The reaction mixture was stirred for 4 h at 25° C., then concentrated under reduced pressure. The residue was dissolved in 50 mL of EtOAc, then was washed with 3×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This resulted in 313 mg (crude) of the title compound as brown oil.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in 50 mL of EtOAc
  4. washwas washed with 3×20 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-44883ca125ab41908e0460fc5452d02b
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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