4-Chloro-3-nitrobenzaldehyde → 8-(4-chloro-3-nitrophenyl)-2,3,4,5,6,8-hexahydro-7H-cyclopenta[b]thieno[2,3-e]pyridin-7-one 1,1-dioxide

HRID 1357731Notes

Reaction equation

HRID 1357731 reaction equation
[CH2:1]1[C:7](=O)[CH2:6][S:3](=[O:5])(=[O:4])[CH2:2]1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19].[NH2:21][C:22]1[CH2:26][CH2:25][C:24](=[O:27])[CH:23]=1>C(O)C>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]2[C:6]3[S:3](=[O:5])(=[O:4])[CH2:2][CH2:1][C:7]=3[NH:21][C:22]3[CH2:26][CH2:25][C:24](=[O:27])[C:23]2=3)=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 855054-Chloro-3-nitrobenzaldehydeHCID 5150067dihydrothiophen-3(2H)-one 1,1-dioxideHCID 122914403-Aminocyclopent-2-en-1-one

Product 1

HCID 99297988-(4-chloro-3-nitrophenyl)-2,3,4,5,6,8-hexahydro-7H-cyclopenta[b]thieno[2,3-e]pyridin-7-one 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of tetrahydrothiophene-3-oxo-1,1-dioxide (171 mg, 1.28 mmol), 4-chloro-3-nitrobenzaldehyde (210 mg, 1.13 mmol) and 3-amino-2-cyclopenten-1-one (110 mg, 1.13 mmol) in ethanol (3 mL) was heated to reflux for 24 hours and cooled. The precipitate was collected, washed with ethanol, dried and recrystallized from methanol/ chloroform to provide the title compound.

Workup

  1. temperatureto reflux for 24 hours
  2. temperaturecooled
  3. customThe precipitate was collected
  4. washwashed with ethanol
  5. customdried
  6. customrecrystallized from methanol/ chloroform

Sources & evidence

ORD record
ord-6e6c15227a8648b692f9ae2c830a73f8
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

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