Triethylamine → HCID 11200699, compound

HRID 1357741Notes

Reaction equation

HRID 1357741 reaction equation
[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[CH2:11]1[C:17](=O)[CH2:16][S:13](=[O:15])(=[O:14])[CH2:12]1.[NH2:19][C:20]1[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH:21]=1.C(N(CC)CC)C>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:7]2[C:21]3[C:22](=[O:26])[CH2:23][CH2:24][CH2:25][C:20]=3[NH:19][C:17]3[CH2:11][CH2:12][S:13](=[O:15])(=[O:14])[C:16]2=3)[CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 728635-BromosalicylaldehydeHCID 788923-Aminocyclohex-2-en-1-oneHCID 5150067dihydrothiophen-3(2H)-one 1,1-dioxide

Product 1

HCID 11200699HCID 11200699, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromosalicylaldehyde (0.201 g, 1.0 mmol), tetrahydrothiophene-3-oxo-1,1-dioxide (0.13 g, 1.0 mmol), 3-amino-2-cyclohexen-1-one (0.11 g, 1.0 mmol) and triethylamine (0.85 mL) were heated in ethanol (4 mL) to 80 ° C. in a sealed tube for 72 hours, cooled, and solvent evaporated. The crude intermediate in ethanol (5 mL) was treated with 1.0 M HCl in ether (1 mL), heated to reflux for 1 hour, cooled, the solid precipitate collected, washed with ethanol and dried to provide 0.13 g of the title compound as an orange-yellow solid.

Workup

  1. temperaturecooled
  2. customsolvent evaporated
  3. additionThe crude intermediate in ethanol (5 mL) was treated with 1.0 M HCl in ether (1 mL)
  4. temperatureheated
  5. temperatureto reflux for 1 hour
  6. temperaturecooled
  7. customthe solid precipitate collected
  8. washwashed with ethanol
  9. customdried

Sources & evidence

ORD record
ord-8e0268ea59be4b3cbfc6dbe2041bb1c0
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

Loading…