Acetic Anhydride → Ethyl 1,2-dimethyl-1,3-benzodiazole-5-carboxylate

HRID 1498892Notes

Reaction equation

HRID 1498892 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[NH:13][CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(=O)(O)[O-].[Na+].[C:20](OC(=O)C)(=O)[CH3:21]>>[CH3:14][N:13]1[C:12]2[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=2[N:1]=[C:20]1[CH3:21]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 2824047Ethyl 3-amino-4-(methylamino)benzoate

Product 1

HCID 12493640Ethyl 1,2-dimethyl-1,3-benzodiazole-5-carboxylate

Procedure

Ethyl 3-amino-4-methylaminobenzoate (1.00 g, 5.15 mmol) prepared in the Step 1-1-3 was dissolved in acetic anhydride (4 ml), and the mixture was heated under reflux for 19 hours. After being allowed to cool, the mixture was neutralized with a saturated sodium bicarbonate solution and subjected to extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (1.15 g, quantitative) as a light-brown oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 19 hours
  3. temperatureto cool
  4. extractionsubjected to extraction with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-eb77b943f797455bb90af7eae8fb00eb
Source dataset
uspto-grants-2015_12
Patent number
US09200008B2

Reaction notes

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