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

HRID 478284Notes

Reaction equation

HRID 478284 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 dried 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
  4. customdried for 16 hours under high vacuum

Sources & evidence

ORD record
ord-c11fe58ca9f342f7a890d8761fafbaa1
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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