Hydrazine hydrate (1:1) → HCID 19956234, compound

HRID 1779491Notes

Reaction equation

HRID 1779491 reaction equation
O.NN.[CH3:4][C:5]1[C:12]2[N:11]3[CH:13]=[CH:14][CH:15]=[C:10]3/[C:9](=[N:16]/[O:17][CH2:18][CH2:19][N:20]3C(=O)C4=CC=CC=C4C3=O)/[C:8]=2[S:7][CH:6]=1>C(O)C.C(O)(C)C>[CH3:4][C:5]1[C:12]2[N:11]3[CH:13]=[CH:14][CH:15]=[C:10]3/[C:9](=[N:16]/[O:17][CH2:18][CH2:19][NH2:20])/[C:8]=2[S:7][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)3×HCID 19956235HCID 19956235, compound

Product 1

HCID 19956234HCID 19956234, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 22179027Isopropanol ethanolSolvent

Procedure

Add 0.3 ml (6.1 mmol) of hydrazine hydrate to a solution of 0.85 g (2.2 mmol) of (Z)-3-methyl-8-[(2-phthalimido-ethoxy)imino]thieno[2,3-d]pyrrolo[1,2-a]pyrrole in 50 ml of a mixture of ethanol/isopropanol, 1:1. The reaction mixture is heated to reflux. After refluxing the mixture for 30 minutes, add 0.3 ml of hydrazine hydrate and heat at reflux again for 90 minutes. Add 0.5 ml of hydrazine hydrate during the course of the 90 minutes' refluxing. After cooling the reaction mixture, the precipitate formed is removed by filtration and the filtrate is concentrated under reduced pressure. The residue is extracted with diethyl ether and the ethereal phase is washed with water, dried over magnesium sulfate, treated with animal charcoal and concentrated to yield 200 mg of the title product in the form of an oil (base).

Workup

  1. temperatureThe reaction mixture is heated to reflux
  2. temperatureAfter refluxing the mixture for 30 minutes
  3. temperatureheat
  4. temperatureat reflux again for 90 minutes
  5. temperaturerefluxing
  6. temperatureAfter cooling the reaction mixture
  7. customthe precipitate formed
  8. customis removed by filtration
  9. concentrationthe filtrate is concentrated under reduced pressure
  10. extractionThe residue is extracted with diethyl ether
  11. washthe ethereal phase is washed with water
  12. dry with materialdried over magnesium sulfate
  13. additiontreated with animal charcoal
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-e1c736f2782b4d27afd1151f59adc020
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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