Thioacetamide → HCID 19775571, compound

HRID 1613230Notes

Reaction equation

HRID 1613230 reaction equation
Cl[CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)[C:3](=O)[CH3:4].[C:16]([NH2:19])(=[S:18])[CH3:17]>C(O)C.CCCCC>[CH3:17][C:16]1[S:18][C:2]([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)=[C:3]([CH3:4])[N:19]=1

Participants

5

Reactant 2

HCID 2723949ThioacetamideHCID 19775550HCID 19775550, compound

Product 1

HCID 19775571HCID 19775571, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8003PentaneSolvent

Procedure

4.7 g of 3-chloro-4-(4-nitrophenyl)butan-2-one and 2.4 g of thioacetamide are dissolved in 60 ml of ethanol and refluxed for 12 hours. The reaction medium is concentrated, the residue is taken up in water and the solution is rendered basic with sodium carbonate and extracted with chloroform. After concentration of the organic phase, the solid obtained is taken up in hot pentane to give 3.5 g of 2,4-dimethyl-5-(4-nitrobenzyl)thiazole in the form of yellow crystals melting at 66° C.

Workup

  1. temperaturerefluxed for 12 hours
  2. concentrationThe reaction medium is concentrated
  3. extractionextracted with chloroform
  4. customAfter concentration of the organic phase, the solid obtained

Sources & evidence

ORD record
ord-3a57211ae5f14641b84657733032337c
Source dataset
uspto-grants-1993_03
Patent number
US05192781

Reaction notes

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