Acetic Acid → HCID 71816076, compound

HRID 532601Notes

Reaction equation

HRID 532601 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1)[C:6]([CH:8]1[CH2:15][C:11]2[S:12][CH:13]=[CH:14][C:10]=2[C:9]1=O)=O.O.[NH2:27][NH2:28].C(O)(=O)C>C(O)C>[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[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:28][N:27]=2)[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:19]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 86699216HCID 86699216, compound

Product 1

HCID 71816076HCID 71816076, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

5-(3,5-Bis-trifluoromethyl-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (1.07 g, 4.1 mmol), hydrazine monohydrate (0.3 mL, 6.2 mmol), glacial acetic acid (0.8 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-(3,5-Bis-trifluoromethyl-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (0.58 g, 1.5 mmol) as white solid in 37% yield.

Workup

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

Sources & evidence

ORD record
ord-7d9709cfee0347f4bf9d5f99ab1fe5f1
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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