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

HRID 532542Notes

Reaction equation

HRID 532542 reaction equation
[C:1]([CH:9]1[CH2:16][C:12]2[S:13][CH:14]=[CH:15][C:11]=2[C:10]1=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:19][NH2:20].C(O)(=O)C>C(O)C>[C:2]1([C:1]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:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 866991985-Benzoyl-5,6-dihydro-cyclopenta[b]thiophen-4-one

Product 1

HCID 718158796-Phenyl-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentaleneYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

5-Benzoyl-5,6-dihydro-cyclopenta[b]thiophen-4-one (2.42 g, 10.0 mmol), hydrazine monohydrate (1.92 mL, 60 mmol), glacial acetic acid (2.7 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-Phenyl-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (2.4 g, 8.0 mmol) as white solid in 80% yield.

Workup

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

Sources & evidence

ORD record
ord-7d01b78b6ee14ac3aa826f1fcf7c8fa4
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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