Semicarbazide hydrochloride → HCID 53896233, compound

HRID 1166304Notes

Reaction equation

HRID 1166304 reaction equation
[CH2:1]1[O:18][C:17]2[CH:16]=[CH:15][C:5]([O:6][C:7]3[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=3)=[CH:4][C:3]=2[O: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[O:18][C:17]2[CH:16]=[CH:15][C:5]([O:6][C:7]3[CH:14]=[CH:13][C:10]([CH:11]=[N:20][NH:21][C:22]([NH2:24])=[O:23])=[CH:9][CH:8]=3)=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 12044475HCID 12044475, compound

Product 1

HCID 53896233HCID 53896233, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 4-(3,4-methylenedioxyphenoxy)benzaldehyde (1.7 g, 7.0 mmol) in ethanol (40 mL) was added a solution of semicarbazide hydrochloride (0.82 g, 7.1 mmol) and sodium acetate (0.55 g, 6.7 mmol) in water (10 mL). The mixture was stirred at room temperature for 30 min. The resulting white solid was collected by filtration, washed with water and dried in vacuo to yield the title compound (1.2 g, 4.0 mmol, 57%), mp: 225-226° C. 1H NMR (DMSO-d6): δ 10.17 (s, 1H), 7.80 (s, 1H), 7.70 (d, J=8.7, 2H), 6.93 (d, J=8.3, 1H), 6.92 (d, J=8.7, 2H), 6.77 (d, J=2.4, 1H), 6.53 (dd, J=2.4, 8.3, 1H), 6.44 (s, 2H), 6.06 (s, 2H).

Workup

  1. filtrationThe resulting white solid was collected by filtration
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-8d7b7851e65a4568a431da31da942a6e
Source dataset
uspto-grants-2003_09
Patent number
US06613803B1

Reaction notes

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