3-Aminocyclohex-2-en-1-one → HCID 10223145, compound

HRID 635993Notes

Reaction equation

HRID 635993 reaction equation
[S:1]1[CH2:6][C:5](=O)[CH2:4][C:3](=[O:8])[CH2:2]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[NH2:19][C:20]1[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH:21]=1>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:21]3[C:22](=[O:26])[CH2:23][CH2:24][CH2:25][C:20]=3[NH:19][C:5]3[CH2:6][S:1][CH2:2][C:3](=[O:8])[C:4]2=3)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

5

Reactant 3

HCID 788923-Aminocyclohex-2-en-1-oneHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 3252862H-Thiopyran-3,5(4H,6H)-dione

Product 1

HCID 10223145HCID 10223145, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of thiopyran-3,5-dione (Fehnel, E. A., J. Amer. Chem. Soc., (1955), 77, 4241-4244) (0.12 g, 1.0 mmol), 3-bromo-4-fluorobenzaldehyde (0.20 g, 1.0 mmol), 3-amino-2-cyclohexene-1-one (0.11 g, 1.0 mmol) and ethanol (5 mL) was heated to 80° C. in a sealed tube for 60 hours and cooled to ambient temperature. The resulting solid was collected by filtration, washed with ethanol and fried for 16 hours under high vacuum to provide the title compound (0.13 g).

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with ethanol and fried for 16 hours under high vacuum

Sources & evidence

ORD record
ord-15ae7579848640eebe0dee04a3cca9b1
Source dataset
uspto-grants-2001_02
Patent number
US06191140B1

Reaction notes

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