Chlorosuccinimide → HCID 178494681, compound

HRID 1488113Notes

Reaction equation

HRID 1488113 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[NH:5][C:6]([C:9]2[C:10]([CH3:20])=[CH:11][C:12]([CH3:19])=[C:13]([CH:18]=2)[C:14]([O:16][CH3:17])=[O:15])=[CH:7][N:8]=1.C1C(=O)N([Cl:28])C(=O)C1>C(Cl)(Cl)Cl>[Cl:28][C:7]1[N:8]=[C:4]([CH2:3][O:2][CH3:1])[NH:5][C:6]=1[C:9]1[C:10]([CH3:20])=[CH:11][C:12]([CH3:19])=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 90033625Methyl 5-(2-(methoxymethyl)-1H-imidazol-5-yl)-2,4-dimethylbenzoate2×

Product 1

HCID 178494681HCID 178494681, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of methyl 5-(2-(methoxymethyl)-1H-imidazol-5-yl)-2,4-dimethylbenzoate (compound 230.5, 70 mg, 0.26 mmol) in chloroform (6 mL). NCS (35 mg, 0.26 mmol) was added to the reaction. The reaction mixture was stirred overnight at room temperature, then quenched with 1 mL of water. The aqueous phase was extracted with 2×5 mL of dichloromethane and the combined organic layers were concentrated under reduced pressure. The residue was applied onto a silica gel chromatography with ethyl acetate/petroleum ether (1:10) as eluent to yield 30 mg (38%) of the title compound as a white crude solid.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customquenched with 1 mL of water
  3. extractionThe aqueous phase was extracted with 2×5 mL of dichloromethane
  4. concentrationthe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-f4e0c7368fda432583ebebe69f4f668b
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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