Semicarbazide → 3,5-Dimethyl-4-(3-isopropyl-4-methoxy-phenoxy)-benzaldehyde-semicarbazone

HRID 1168102Notes

Reaction equation

HRID 1168102 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[O:7][C:8]1[C:15]([CH3:16])=[CH:14][C:11]([CH:12]=O)=[CH:10][C:9]=1[CH3:17])([CH3:3])[CH3:2].[NH2:23][NH:24][C:25]([NH2:27])=[O:26].C([O-])(=O)C.[Na+]>C(O)C>[CH3:16][C:15]1[CH:14]=[C:11]([CH:10]=[C:9]([CH3:17])[C:8]=1[O:7][C:6]1[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:4]([CH:1]([CH3:2])[CH3:3])[CH:5]=1)[CH:12]=[N:23][NH:24][C:25]([NH2:27])=[O:26]

Participants

5

Reactant 3

HCID 5196SemicarbazideHCID 517045Sodium AcetateHCID 222856654-(3-Isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-benzaldehyde

Product 1

HCID 697550043,5-Dimethyl-4-(3-isopropyl-4-methoxy-phenoxy)-benzaldehyde-semicarbazoneYield 89.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(3-isopropyl-4-methoxy-phenoxy)-3,5-dimethyl-benzaldehyde (19 mg, 0.063 mmol) in ethanol (1 ml) at room temperature was added semicarbazide (7.7 mg, 0.69 mmol) and sodium acetate (5.1 mg, 0.063 mmol). After stirring at room temperature for about one hour, the solvent was removed under vacuum, and the residue was dissolved in ethyl acetate (5 ml). The ethyl acetate solution was washed with water (3×5 ml), brine (5 ml), dried, filtered, and concentrated to afford the title compound (20 mg) as a yellow solid which was used directly in the next step without further purification. MS (APCl−) Calc: 355.2, found: 354.3 (M−1).

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionthe residue was dissolved in ethyl acetate (5 ml)
  3. washThe ethyl acetate solution was washed with water (3×5 ml), brine (5 ml)
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0c06e22458e54330992a8dcce0ddb85a
Source dataset
uspto-grants-2003_09
Patent number
US06620830B2

Reaction notes

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