Semicarbazide hydrochloride → HCID 54034523, compound

HRID 1166307Notes

Reaction equation

HRID 1166307 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl.[NH2:20][NH:21][C:22]([NH2:24])=[O:23].C([O-])(=O)C.[Na+]>C(O)C.O>[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[N:20][NH:21][C:22]([NH2:24])=[O:23])=[CH:13][CH:12]=3)=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 23433269HCID 23433269, compound

Product 1

HCID 54034523HCID 54034523, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(5-indanoxy)benzaldehyde (6.2 g) in ethanol (100 mL) was added a solution of semicarbazide hydrochloride (3.2 g) and sodium acetate (2.3 g) in water (50 mL) at room temperature. The mixture was stirred for 1 h, and the resulting solid was collected by filtration, washed with water (3×100 mL) and dried in vacuo to yield the title compound as a pale yellow solid (7.5 g, 97%), mp: 218-220° C. 1H NMR (DMSO-d6): δ 10.19 (s, 1H), 7.80 (s, 1H), 7.70 (d, J=8.7, 2H), 7.24 (d, J=8.1, 1H), 6.94 (d, J=8.7, 2H), 6.92 (s, 1H), 6.82 (d, J=8.1, 1H), 6.45 (s, 2H), 2.84 (t, J=7.5, 4H), 2.05 (m, 2H).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water (3×100 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-37c50fcf7c06480895d6f3ed3a06b355
Source dataset
uspto-grants-2003_09
Patent number
US06613803B1

Reaction notes

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