Acetic Acid → HCID 71816078, compound

HRID 532597Notes

Reaction equation

HRID 532597 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([CH:8]2[CH2:15][C:11]3[S:12][CH:13]=[CH:14][C:10]=3[C:9]2=O)=O)=[CH:4][CH:3]=1.O.[NH2:20][NH2:21].C(O)(=O)C>C(O)C>[F:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[C:8]3[CH2:15][C:11]4[S:12][CH:13]=[CH:14][C:10]=4[C:9]=3[NH:21][N:20]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 86699215HCID 86699215, compound

Product 1

HCID 71816078HCID 71816078, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

5-(4-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol), hydrazine monohydrate (0.15 mL, 3.1 mmol), glacial acetic acid (0.5 mL) and ethanol (10 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-(4-Fluoro-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.45 g, 1.7 mmol) as yellow solid in 81% yield.

Workup

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

Sources & evidence

ORD record
ord-71eea26a98934370b4c7c9bc8f044eb1
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

Loading…