O-Phenylenediamine → 2H-1,5-Benzodiazepin-2-one, 4-ethoxy-1,3-dihydro-

HRID 914701

Reaction equation

HRID 914701 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH2:9]([O:11][C:12](=O)[CH:13]=[C:14](OCC)[O:15]CC)[CH3:10]>C(O)(=O)C>[CH2:9]([O:11][C:12]1[CH2:13][C:14](=[O:15])[NH:8][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[N:7]=1)[CH3:10]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 1693882-Propenoic acid, 3,3-diethoxy-, ethyl ester

Product 1

HCID 589579152H-1,5-Benzodiazepin-2-one, 4-ethoxy-1,3-dihydro-Yield 56.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
140 °C

Procedure

To a solution phenylenediamine (17.2 g, 159.2 mmol) and acetic acid (0.4 mL) in xylenes (225 mL) at 140° C. was added 3,3-diethoxyacrylic acid ethyl ester (30.0 g, 159.2 mmol) in xylenes (80 mL) dropwise over 50 minutes. The reaction was heated at 140° C. for 2 hours, was cooled to room temperature, and was stirred for 24 h. The resulting white precipitate was filtered, was washed with ether (100 mL), and was dried under vacuum to provide 18.37 g of 4-ethoxy-1,3-dihydro-benzo[b][1,4]diazepin-2-one as a white fluffy solid. MS 205 (M+1).

Workup

  1. temperaturewas cooled to room temperature
  2. filtrationThe resulting white precipitate was filtered
  3. washwas washed with ether (100 mL)
  4. customwas dried under vacuum

Sources & evidence

ORD record
ord-212100e82c624273907b2684f40afc23
Source dataset
uspto-grants-2007_09
Patent number
US07265104B2

Linked notes

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