Acetic Acid → HCID 71816077, compound

HRID 532607Notes

Reaction equation

HRID 532607 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([CH:7]1[CH2:14][C:10]2[S:11][CH:12]=[CH:13][C:9]=2[C:8]1=O)=O.O.[NH2:20][NH2:21].C(O)(=O)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:5]2[C:7]3[CH2:14][C:10]4[S:11][CH:12]=[CH:13][C:9]=4[C:8]=3[NH:21][N:20]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 86699218HCID 86699218, compound

Product 1

HCID 71816077HCID 71816077, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

5-(3-Bromo-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (2.5 g, 8.2 mmol), hydrazine monohydrate (0.6 mL, 12 mmol), glacial acetic acid (1.5 mL) and ethanol (30 mL) were 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-(3-Bromo-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.8 g, 2.5 mmol) as white solid in 30% yield.

Workup

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

Sources & evidence

ORD record
ord-eb1e990b85964c42b4bfef93d71cb6dd
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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