Ethanol → HCID 140490822, compound

HRID 860427Notes

Reaction equation

HRID 860427 reaction equation
O.[NH2:2][NH2:3].C(O)C.Cl.[NH2:8][N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=O)[CH3:15]>O>[NH2:8][N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1/[C:14](=[N:2]/[NH2:3])/[CH3:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 57444538HCID 57444538, compound

Product 1

HCID 140490822HCID 140490822, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, hydrazine monohydrate (530 g) was added to ethanol (1.7 L) over 55 minutes. To the mixture was added 1-(1-amino-1H-pyrrol-2-yl)ethanone hydrochloride (170 g) over 20 minutes. The mixture was stirred for 10 minutes at room temperature and heated to refluxing temperature over 55 minutes, and refluxed for 15 minutes. After cooling the mixture under a water bath, water (1.7 L) was added to the mixture (30 to 31° C.). Ethanol was evaporated off, and the resulting mixture was extracted with chloroform (0.85×4 mL). The combined organic extract was washed with brine (1.3 L). The brine was extracted with chloroform (0.85 L). The combined organic extract was dried over anhydrous magnesium sulfate, and evaporated to give (1E)-1-(1-amino-1H-pyrrol-2-yl)ethanone hydrazone as a brown crystal (112 g).

Workup

  1. temperatureheated
  2. temperatureto refluxing temperature over 55 minutes
  3. temperaturerefluxed for 15 minutes
  4. temperatureAfter cooling the mixture under a water bath
  5. customEthanol was evaporated off
  6. extractionthe resulting mixture was extracted with chloroform (0.85×4 mL)
  7. extractionThe combined organic extract
  8. washwas washed with brine (1.3 L)
  9. extractionThe brine was extracted with chloroform (0.85 L)
  10. extractionThe combined organic extract
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. customevaporated

Sources & evidence

ORD record
ord-41f5523d81c146609c1865b897661bfc
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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