Acetic Acid → 4-Acetamido-3-iodobenzaldehyde thiosemicarbazone

HRID 1168151Notes

Reaction equation

HRID 1168151 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].C(O)(=O)C.[C:10]([NH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][C:15]=1[I:22])(=[O:12])[CH3:11]>O.C(O)C>[C:10]([NH:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[N:1][NH:2][C:3]([NH2:5])=[S:4])=[CH:16][C:15]=1[I:22])(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2723789ThiosemicarbazideHCID 229919464-Acetamido-3-iodobenzaldehyde

Product 1

HCID 30022964-Acetamido-3-iodobenzaldehyde thiosemicarbazone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.728 g (0.008 mole) of thiosemicarbazide (Aldrich T3,340-5) in 25 mL of water containing 1.6 mL of glacial acetic acid was added to a solution of 2.319 (0.008 mole) of 4-acetamido-3-iodobenzaldehyde (33) in 40 mL of absolute ethanol (heating was required to make this dissolve) at 80°. The mixture was stirred at this temperature for 45 minutes. A white precipitate developed in the solution which was filtered after cooling the reaction mixture to give 2.55 (88%) of 34 as white crystals, mp 241-43° (dec.). Infrared (IR) and NMR analysis gave the following results:

Workup

  1. temperatureheating
  2. dissolutionthis dissolve) at 80°
  3. filtrationwas filtered
  4. temperatureafter cooling the reaction mixture

Sources & evidence

ORD record
ord-bc7a04b2cf924c4fb493f29e59bbb586
Source dataset
uspto-grants-2003_09
Patent number
US06624153B2

Reaction notes

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