Semicarbazide hydrochloride → HCID 54073531, compound

HRID 1166303Notes

Reaction equation

HRID 1166303 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.Cl.[NH2:17][NH:18][C:19]([NH2:21])=[O:20].C([O-])(=O)C.[Na+]>C(O)C.O.C(OCC)(=O)C>[N:1]1[CH:6]=[CH:5][C:4]([O:7][C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[N:17][NH:18][C:19]([NH2:21])=[O:20])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 11236Semicarbazide hydrochlorideHCID 517045Sodium AcetateHCID 12084914HCID 12084914, compound

Product 1

HCID 54073531HCID 54073531, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(4-pyridinoxy)benzaldehyde (570 mg, 2.86 mmol) in ethanol (10 mL) was added a solution of semicarbazide hydrochloride (350 mg, 3.03 mmol) and sodium acetate (235 mg, 2.86 mmol) in water (5 mL). The mixture was stirred at room temperature for 30 min., diluted with ethyl acetate (75 mL), washed with 2N NaOH, water and brine, dried over Na2SO4, concentrated in vacuo to yield the title compound as a white solid (720 mg, 2.77 mmol, 97%), mp: 212-213° C. 1H NMR (DMSO-d6): δ 10.29 (s, 1H), 8.49 (d, J=4.9, 2H), 7.87 (s, 1H), 7.84 (d, J=8.5, 2H), 7.19 (d, J=8.5, 2H), 6.96 (d, J=4.9, 2H), 6.53 (s, 2H).

Workup

  1. washwashed with 2N NaOH, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-08f6890cbc274b9fa00c3ce6c259bdcc
Source dataset
uspto-grants-2003_09
Patent number
US06613803B1

Reaction notes

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