Methanol → HCID 18961689, compound

HRID 249196Notes

Reaction equation

HRID 249196 reaction equation
[Cl:1]OC(C)(C)C.[CH:7]([C:10]1([CH3:26])[C:14](=[O:15])[NH:13][C:12]([C:16]2[N:25]=[CH:24][CH:23]=[CH:22][C:17]=2[C:18]([O:20][CH3:21])=[O:19])=[N:11]1)([CH3:9])[CH3:8].CO>C(Cl)Cl>[Cl:1][N:13]1[C:14](=[O:15])[C:10]([CH:7]([CH3:9])[CH3:8])([CH3:26])[N:11]=[C:12]1[C:16]1[N:25]=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 521297Tert-Butyl hypochloriteHCID 13246868HCID 13246868, compound

Product 1

HCID 18961689HCID 18961689, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl hypochlorite (5.92 g, 0.0545 mol) is added to a solution of methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate (10.0 g, 0.0363 mol) and methanol. The reaction mixture is covered with foil and stirring is continued for 1 day. The reaction mixture is concentrated in vacuo to give a liquid. The liquid is dissolved into methylene chloride, dried over anhydrous magnesium sulfate and concentrated in vacuo to yield a yellow syrup. The yellow syrup is chromatographed using silica gel and 5% ethyl acetate in hexanes as eluent to give the title compound as a colorless syrup (7.16 g, 64%), identified by IR and NMR spectral analyses.

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. customto give a liquid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto yield a yellow syrup
  6. customThe yellow syrup is chromatographed

Sources & evidence

ORD record
ord-5b0625efff1647cea3feb0ae4c8f0538
Source dataset
uspto-grants-1993_05
Patent number
US05213607

Reaction notes

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