Acetic Acid → HCID 71816083, compound

HRID 532619Notes

Reaction equation

HRID 532619 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[C:17]([Cl:19])[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.[NH2:21][NH2:22].C(O)(=O)C>C(O)C>[Cl: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:22][N:21]=2)[CH:16]=[C:17]([Cl:19])[CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 86699220HCID 86699220, compound

Product 1

HCID 71816083HCID 71816083, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

5-(3,5-Dichloro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (1.5 g, 4.8 mmol), hydrazine monohydrate (0.35 mL, 7.2 mmol), glacial acetic acid (0.8 mL) and ethanol (15 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-(3,5-Dichloro-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (1.33 g, 4.3 mmol) as yellow solid in 90% yield.

Workup

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

Sources & evidence

ORD record
ord-f235181dea6d4c11904146ab2f1e4cf6
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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