Benzoylhydrazine → N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide

HRID 900130Notes

Reaction equation

HRID 900130 reaction equation
C(O[C:4]1[CH2:10][C:9](=[O:11])[N:8]([CH2:12][C:13]([N:15]([CH:22]([CH3:24])[CH3:23])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[C:7]2[CH:25]=[CH:26][CH:27]=[CH:28][C:6]=2[N:5]=1)C.[C:29]([NH:37][NH2:38])(=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC(O)=O.C(Cl)Cl>[CH:22]([N:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:13](=[O:14])[CH2:12][N:8]1[C:9](=[O:11])[CH2:10][C:4]2[N:5]([C:29]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:37][N:38]=2)[C:6]2[CH:28]=[CH:27][CH:26]=[CH:25][C:7]1=2)([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 11955BenzoylhydrazineHCID 589579362-(4-ethoxy-2-oxo-2,3-dihydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide2×

Product 1

HCID 58957944N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(4-ethoxy-2-oxo-2,3-dihydro-benzo[b][1,4]diazepin-1-yl)-N-isopropyl-N-phenyl-acetamide (Preparation 5(B) (71.14 g, 0.187 mol) in 1.04 L of AcOH was added benzoic acid hydrazide (27.28 g, 0.196 mol) in one portion. The reaction was heated to 80° C. and was stirred for 4 hours. The reaction was cooled to room temperature and the AcOH was removed in vacuo to give an off-white solid. The solid was dissolved in 1 L of methylene chloride. The organic solution was washed with 1 L of saturated NaHCO3 solution followed by brine and was dried over Na2SO4. The methylene chloride solution was diluted with an equal volume of methyl tert-butyl ether and the resulting solution was concentrated in vacuo to low volume causing a white solid to precipitate. The precipitate was collected on a sintered glass funnel and was rinsed with methyl tert-butyl ether. The solid was dried in vacuo to give 81.41 g of N-isopropyl-2-(5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl)-N-phenyl-acetamide as a white solid. 1H NMR (CD2Cl2) δ 7.57-7.35 (m, 10H), 7.27 (br s, 1H), 7.21 (br s, 1H), 7.10 (t, 1H), 6.87 (d, 1H), 4.89 (m, 1H), 4.19-3.99 (m, 3H), 3.53 (d, 1H), 1.03 (m, 6H); MS 452.3 (M+1), 450.5 (M−1).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe AcOH was removed in vacuo
  3. customto give an off-white solid
  4. washThe organic solution was washed with 1 L of saturated NaHCO3 solution
  5. dry with materialwas dried over Na2SO4
  6. additionThe methylene chloride solution was diluted with an equal volume of methyl tert-butyl ether
  7. concentrationthe resulting solution was concentrated in vacuo to low volume
  8. customto precipitate
  9. customThe precipitate was collected on a sintered glass funnel
  10. washwas rinsed with methyl tert-butyl ether
  11. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-328c544e982044668349fa9082284304
Source dataset
uspto-grants-2008_04
Patent number
US07358242B2

Reaction notes

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