Acetic Acid → 3-(1,2,3,4-Tetrahydronaphthalen-1-YL)-3H-imidazole-4-carboxylic acid methyl ester

HRID 5768Notes

Reaction equation

HRID 5768 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([CH:18]=O)[N:5]([CH:16]=O)[CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1.C([O-])(=O)C.[NH4+:25].C(O)(=O)C>O>[CH3:1][O:2][C:3]([C:4]1[N:5]([CH:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][CH2:8][CH2:7]2)[CH:16]=[N:25][CH:18]=1)=[O:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium Acetate2×HCID 19794118N,alpha-bis-formyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)glycine methyl ester

Product 1

HCID 144976243-(1,2,3,4-Tetrahydronaphthalen-1-YL)-3H-imidazole-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 16.5 g of N,α-bis-formyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl) glycine methyl ester, 65.0 g of ammonium acetate and 100 ml of acetic acid are refluxed for 8 hours. Then additional 50 g ammonium acetate are added and the refluxing is continued for further 4 hours. The solution is diluted with 300 ml of water and extracted twice, with 100 ml of toluene each time. The organic phases are combined, concentrated and separated at silica gel by chromatography. Concentration of the eluate yields 1-(1,2,3,4-tetrahydronaphthalen-1-yl) -5-imidazolecarboxylic acid methyl ester, having a melting point of 63° C.

Workup

  1. temperatureare refluxed for 8 hours
  2. extractionextracted twice, with 100 ml of toluene each time
  3. concentrationconcentrated
  4. customseparated at silica gel by chromatography

Sources & evidence

ORD record
ord-f57d7a6d780c4a4a823cce69c82616b4
Source dataset
uspto-grants-1993_09
Patent number
US05246915

Reaction notes

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