1-Acetyl-4-methylimidazole → HCID 70417175, compound

HRID 868270Notes

Reaction equation

HRID 868270 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:6]2.C([N:20]1[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]1)(=O)C>C(#N)C>[CH3:25][C:23]1[NH:22][C:21]([CH2:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[CH:9]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:7]=[CH:6]3)=[N:20][CH:24]=1

Participants

4

Reactant 2

HCID 109534921-Acetyl-4-methylimidazoleHCID 13715274HCID 13715274, compound

Product 1

HCID 70417175HCID 70417175, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2 g (7.16 mmol) of methyl 6-bromomethyl-2-naphthoate and 1.07 g (8.6 mmol) of 1-acetyl-4-methylimidazole are heated under reflux in absolute acetonitrile (8 hours). After the reaction solution has been evaporated, the residue is taken up in 2N HCl, and the solution is extracted with ethyl acetate. The ethyl acetate phases are discarded. After the aqueous phase has been neutralized with sodium carbonate, it is extracted with ethyl acetate, and the ethyl acetate phase is dried and evaporated in vacuo. 1.4 g (70%) of methyl 6-(5-methyl-1-imidazolylmethyl)-2-naphthoate are obtained by trituration of the residue with ether. Melting point 101°-102° C.

Workup

  1. customAfter the reaction solution has been evaporated
  2. extractionthe solution is extracted with ethyl acetate
  3. extractionis extracted with ethyl acetate
  4. dry with materialthe ethyl acetate phase is dried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-2392eb4dea0d45b3ac2eac9cd6abbac1
Source dataset
uspto-grants-1988_10
Patent number
US04778817

Reaction notes

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