Imidazole → HCID 20248316, compound

HRID 1589161Notes

Reaction equation

HRID 1589161 reaction equation
Cl[CH2:2][C:3]([N:5]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[CH3:23])[CH:6]([CH2:11][CH3:12])[C:7]([O:9][CH3:10])=[O:8])=[O:4].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1>CN(C)C=O>[N:24]1([CH2:2][C:3]([N:5]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[CH3:23])[CH:6]([CH2:11][CH3:12])[C:7]([O:9][CH3:10])=[O:8])=[O:4])[CH:28]=[CH:27][N:26]=[CH:25]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 13117217HCID 13117217, compound

Product 1

HCID 20248316HCID 20248316, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12 g (0.036 mole) of methyl 2-(N-chloroacetyl-2-methylnaphth-1-ylamino)-butyrate (Example 1) were dissolved in 60 ml of dry N,N-dimethylformamide, and the solution was stirred with 7.3 g (0.108 mole) of imidazole at 70° C. for 10 hours. The mixture was concentrated under reduced pressure, and the residue was extracted by shaking with 150 ml of methylene chloride and 50 ml of water. The organic layer was separated off, washed with twice 50 ml of water, dried over sodium sulfate, and concentrated under reduced pressure. 8 g (61.6% of theory) of methyl 2-[N-(imidazol-1-ylacetyl)-2-methylnaphth-1-ylamino]-butyrate were obtained as a yellowish resin (compound No. 2).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionthe residue was extracted
  3. customThe organic layer was separated off
  4. washwashed with twice 50 ml of water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3a26950690774ec894d192307933c14c
Source dataset
uspto-grants-1986_02
Patent number
US04568684

Reaction notes

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