Chlorosuccinimide → HCID 178494680, compound

HRID 1487877Notes

Reaction equation

HRID 1487877 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[NH:5][C:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][N:8]=1.C1C(=O)N([Cl:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Cl:27][C:7]1[N:8]=[C:4]([CH2:3][O:2][CH3:1])[NH:5][C:6]=1[C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[CH3:19])[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 90030068Methyl 3-(2-(methoxymethyl)-1H-imidazol-5-yl)-4-methylbenzoate2×

Product 1

HCID 178494680HCID 178494680, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

Into a 50-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methyl 3-(2-(methoxymethyl)-1H-imidazol-5-yl)-4-methylbenzoate (compound 27.3, 40 mg, 0.15 mmol) and NCS (24.6 mg, 0.18 mmol) in CCl4 (20 mL). The resulting mixture was stirred for 2 h at 50° C., then cooled to room temperature and quenched with water (100 mL). The aqueous phase was extracted with ethyl acetate (100 mL) and the combined organic layers were washed with brine (3×30 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to yield 30 mg (crude) of the title compound as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, which was purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperaturecooled to room temperature
  4. customquenched with water (100 mL)
  5. extractionThe aqueous phase was extracted with ethyl acetate (100 mL)
  6. washthe combined organic layers were washed with brine (3×30 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70fa8efbc7a44b7aaa812d9671d1a937
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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