Ethanol → HCID 178519438, compound

HRID 1266022Notes

Reaction equation

HRID 1266022 reaction equation
C(OC(OCC)[C:5]1[CH:6]=[C:7]([C:11]2[N:16]3[CH2:17][CH2:18][C:19]4[NH:20][C:21](=[O:24])[CH:22]=[CH:23][C:14]([C:15]=43)=[CH:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1)C.S(=O)(=O)(O)O.C[CH2:34][OH:35]>O>[O:24]=[C:21]1[NH:20][C:19]2[CH2:18][CH2:17][N:16]3[C:11]([C:7]4[CH:6]=[CH:5][C:10]([CH:34]=[O:35])=[CH:9][CH:8]=4)=[N:12][CH:13]=[C:14]([C:15]=23)[CH:23]=[CH:22]1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 69702690HCID 69702690, compound

Product 1

HCID 178519438HCID 178519438, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(3-Diethoxymethyl-phenyl)-8,9-dihydro-7H-2,7,9a-triaza-benzo[cd]azulen-6-one (0.79 g, 2.18 mmol) was dissolved in EtOH (22 mL) and water (22 mL). Concentrated sulfuric acid (0.5 mL) was added, and the reaction brought to reflux for 5 h. The reaction mixture was cooled to rt, and the EtOH removed in vacuo. The residue was diluted with saturated NaHCO3, and the resulting solids were filtered and washed with water, then dried under vacuum overnight to produce 0.47 g (74%) of white solid: 1H NMR (DMSO-d6) δ 3.54-3.55 (m, 2H), 4.50-4.51 (m, 2H), 7.39 (t, 1H, J=7.8 Hz), 7.88-7.96 (m, 2H), 8.09-8.10 (m, 4H), 8.46-8.50 (m, 1H), 10.13 (s, 1H).

Workup

  1. temperatureto reflux for 5 h
  2. customthe EtOH removed in vacuo
  3. additionThe residue was diluted with saturated NaHCO3
  4. filtrationthe resulting solids were filtered
  5. washwashed with water
  6. customdried under vacuum overnight

Sources & evidence

ORD record
ord-803ad5fc2da94a83b97ff6e0cc6f4ec5
Source dataset
uspto-grants-2003_04
Patent number
US06548494B1

Reaction notes

Loading…