Triethylamine → HCID 18187088, compound

HRID 1357754Notes

Reaction equation

HRID 1357754 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[CH:7]=O)([O-:3])=[O:2].[CH2:16]1[C:22](=O)[CH2:21][S:18](=[O:20])(=[O:19])[CH2:17]1.[NH2:24][C:25]1[CH2:30][CH2:29][CH2:28][C:27](=[O:31])[CH:26]=1.C(N(CC)CC)C>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]2[C:26]3[C:27](=[O:31])[CH2:28][CH2:29][CH2:30][C:25]=3[NH:24][C:22]3[CH2:16][CH2:17][S:18](=[O:20])(=[O:19])[C:21]2=3)[CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 788923-Aminocyclohex-2-en-1-oneHCID 5150067dihydrothiophen-3(2H)-one 1,1-dioxideHCID 111277623-NITRO-4-(TRIFLUOROMETHYL)BENZALDEHYDE&

Product 1

HCID 18187088HCID 18187088, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 3-Nitro-4-trifluoromethylbenzaldehyde (0.33 g, 1.5 mmol) (Clark, J. Fluorine Chem. 1990, 50, 411), tetrahydrothiophene-3-oxo-1,1-dioxide (0.2 g, 1.5 mmol) and 3-amino-2-cyclohexene-1-one(0. 17 g, 1.5 mmol) in ethanol (2 mL) were heated at reflux for 48 hours with triethylamine (0.1 mL). The reaction mixture was evaporated in vacuo and the residue was chromatographed on silica gel, eluting with 10% ethanol/methylene 25 chloride to afford 0.32 g of the intermediate hemiaminal that was suspended in ethanol (10 mL) and heated at reflux for 2 hours with 2 mL of I M HCUether. The reaction mixture was cooled and the precipitate collected to provide 0.24 g of the title compound.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel
  3. washeluting with 10% ethanol/methylene 25 chloride

Sources & evidence

ORD record
ord-75d3b8fb9cec4123b79a8cd3217f49e5
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

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