Acetic Acid → HCID 3002295, compound

HRID 1168149Notes

Reaction equation

HRID 1168149 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[Cl: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[Cl:22])(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2723789ThiosemicarbazideHCID 22991945N-(2-Chloro-4-formylphenyl)acetamide

Product 1

HCID 3002295HCID 3002295, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.73 g (0.008 mole) of thiosemicarbazide (Aldrich T3,340-5) in 24 mL of water containing 1.6 mL of glacial acetic acid was added to a solution of 1.58 g of (0.008 mole) 4-acetamido-3-chlorobenzaldehyde (24) in 20 mL of ethanol at 700. The mixture was stirred at this temperature for 45 minutes. A white precipitate developed in the reaction mixture, which was filtered after cooling to give 1.95 g (90%) of 25 as off white crystals, mp 235-238°. Infrared (IR) and NMR analysis gave the following results:

Workup

  1. filtrationwas filtered
  2. temperatureafter cooling

Sources & evidence

ORD record
ord-33d7ea83a303449fbba95b213c4746cc
Source dataset
uspto-grants-2003_09
Patent number
US06624153B2

Reaction notes

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