Acetic Acid → HCID 22559539, compound

HRID 983353Notes

Reaction equation

HRID 983353 reaction equation
[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)=[O:11])=[N:6][CH:5]=1)([CH3:3])[CH3:2].C(O)(=O)C.O>C(O)C.[Fe]>[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)=[O:11])=[N:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 22559602HCID 22559602, compound

Product 1

HCID 22559539HCID 22559539, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.55 g (5.05 mmol) of (5-isopropyl-1,3-thiazol-2-yl)-N′-(3-nitrophenyl)urea prepared as described in example 5 and 0.98 g ((17.7 mmol) of iron dust with 2.02 ml (35.35 mmol) of glacial acetic acid in 50 ml of ethanol was stirred at reflux under argon atmosphere. After 5 hours 1.5 l of water was added and the product extracted with ethylacetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated. The residue was finally purified by chromatography on a silica gel column (chloroform/methanol 47/3) giving 0.84 g of the title compound as a white solid.

Workup

  1. customprepared
  2. temperatureat reflux under argon atmosphere
  3. extractionthe product extracted with ethylacetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was finally purified by chromatography on a silica gel column (chloroform/methanol 47/3)

Sources & evidence

ORD record
ord-856fc424181043eda437719c61ff25b1
Source dataset
uspto-grants-2005_03
Patent number
US06863647B2

Reaction notes

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