Water → 3-Ethyl-5-methyl-2-naphthalen-1-yl-3h-imidazole-4-carboxylic acid ethyl ester

HRID 12471Notes

Reaction equation

HRID 12471 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2].[H-].[Na+].[CH2:24](I)[CH3:25].O>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:24][CH3:25])[C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[N:9][C:10]=1[CH3:11])=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[N:9]([CH2:24][CH3:25])[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178470380HCID 178470380, compound

Product 2

HCID 593386983-Ethyl-5-methyl-2-naphthalen-1-yl-3h-imidazole-4-carboxylic acid ethyl esterHCID 686280551-Ethyl-5-methyl-2-naphthalen-1-yl-1h-imidazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-methyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester (1.5 g) in DMF (30 ml) is added NaH (320 mg, 60%) at rt. The solution is stirred for 30 min, and EtI (0.6 ml) is added. After 30 min, the mixture is cooled to 0° C. and H2O is added. The mixture is then extracted with EtOAc. The extracts are combined, dried, evaporated and purified by column (EtOAc:Hexanes 1:1) to give 3-ethyl-5-methyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester [LCMS 309.4 (M+1); δ 4.10 ppm (CH2CH3)] and its regioisomer 1-ethyl-5-methyl-2-naphthalen-1-yl-1H-imidazole-4-carboxylic acid ethyl ester [LCMS 309.4 (M+1); δ 3.72 ppm (CH2CH3)].

Workup

  1. waitAfter 30 min
  2. extractionThe mixture is then extracted with EtOAc
  3. customdried
  4. customevaporated
  5. custompurified by column (EtOAc:Hexanes 1:1)

Sources & evidence

ORD record
ord-6865d417dc3a4acbabe299198449a15e
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Reaction notes

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