Acetic Acid → HCID 19016771, compound

HRID 1728947Notes

Reaction equation

HRID 1728947 reaction equation
[N+](=[CH2:3])=[N-].[CH2:4]([C:11]1[NH:12][C:13]([C:20]([O:22][CH3:23])=[O:21])=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(O)(=O)C>CCOCC>[CH3:3][N:15]1[C:14]([C:16]([O:18][CH3:19])=[O:17])=[C:13]([C:20]([O:22][CH3:23])=[O:21])[N:12]=[C:11]1[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550Diazomethane2×HCID 19016775HCID 19016775, compound

Product 1

HCID 19016771HCID 19016771, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (1.5 g, 35.7 mmol) in ether (100 ml) was slowly added at 0° C. with stirring to a suspension of the above ester (18.59 mmol) in ether (100 mL). After the addition was completed, the solution was stirred at room temperature overnight. Excess diazomethane was decomposed by the slow and careful addition of dilute acetic acid and the mixture was concentrated in vacuo. Water (50 mL) was added and the mixture was thoroughly extracted with dichloromethane. The organic phase was washed with water, saturated sodium bicarbonate and again with water. The solution was dried and the solvent was removed in vacuo to give dimethyl 1-methyl-2-benzyl-4,5-imidazole dicarboxylate.

Workup

  1. additionAfter the addition
  2. concentrationthe mixture was concentrated in vacuo
  3. additionWater (50 mL) was added
  4. extractionthe mixture was thoroughly extracted with dichloromethane
  5. washThe organic phase was washed with water, saturated sodium bicarbonate and again with water
  6. customThe solution was dried
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f305e4805b8245c7ae4a1618b6ff76b2
Source dataset
uspto-grants-1994_07
Patent number
US05329012

Reaction notes

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