Acetic Acid → 6-Pyridin-3-yl-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene

HRID 532569

Reaction equation

HRID 532569 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([CH:9]2[CH2:16][C:12]3[S:13][CH:14]=[CH:15][C:11]=3[C:10]2=O)=O)[CH:2]=1.O.[NH2:19][NH2:20].C(O)(=O)C>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:9]3[CH2:16][C:12]4[S:13][CH:14]=[CH:15][C:11]=4[C:10]=3[NH:20][N:19]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 866992085-(Pyridine-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one

Product 1

HCID 718159466-Pyridin-3-yl-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentaleneYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

5-(Pyridine-3-carbonyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (1.23 g, 5 mmol), hydrazine monohydrate (0.38 mL, 7.5 mmol), glacial acetic acid (0.9 mL) and ethanol (15 mL) was heated at 100° C. under nitrogen for 4 hr. The mixture was cooled to 25° C. and concentrated under reduced pressure to give a solid which was recrystallized from ethanol to provide the corresponding 6-Pyridin-3-yl-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.5 g, 2 mmol) as white solid in 40% yield.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a solid which
  3. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-cfd339aaeb424e29881cb8278b937020
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Linked notes

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