Acetic Acid → HCID 178489130, compound

HRID 532540Notes

Reaction equation

HRID 532540 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=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.[NH2:23][NH2:24].C(O)(=O)C>C(O)C>[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[C:5]1[C:7]2[CH2:14][C:10]3[S:11][CH:12]=[CH:13][C:9]=3[C:8]=2[NH:24][N:23]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 866991975-(2,4-Dimethoxy-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one

Product 1

HCID 178489130HCID 178489130, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

5-(2,4-Dimethoxy-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (1.12 g, 3.69 mmol), hydrazine monohydrate (0.7 mL, 22 mmol), glacial acetic acid (0.6 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-(2,4-Dimethoxy-phenyl)-4,7-dihydro-1-thia-4,5-diaza-cyclopenta[a]pentalene (2.5 g, 3.1 mmol) as yellow solid in 85% yield.

Workup

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

Sources & evidence

ORD record
ord-723ad6da52714fa5b2ff64f05d18c57a
Source dataset
uspto-grants-2014_10
Patent number
US08853207B2

Reaction notes

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