Undecane → 2,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamide

HRID 1282427Notes

Reaction equation

HRID 1282427 reaction equation
CCCCCCCCCCC.[C:12]([CH2:14][CH2:15][NH:16][C:17](=[O:36])[C:18]#[C:19][C:20]([CH2:34][F:35])([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1)[CH2:21][F:22])#[N:13]>>[F:22][CH2:21][C:20]1([CH2:34][F:35])[CH:19]=[C:18]([C:17]([NH:16][CH2:15][CH2:14][C:12]#[N:13])=[O:36])[C:29]2[CH:28]=[C:27]([C:30]([F:33])([F:32])[F:31])[CH:26]=[CH:25][C:24]=2[O:23]1

Participants

3

Reactant 2

HCID 14257UndecaneHCID 18424403N-(2-cyanoethyl)-5-fluoro-4-fluoromethyl-4-(4-trifluoromethylphenoxy)-2-pentynamide

Product 1

HCID 99507522,2-bis(fluoromethyl)-N-(2-cyanoethyl)-6-trifluoromethyl-2H-1-benzopyran-4-carboxamideYield 90%

Procedure

To undecane (0.8 ml) being heated under reflux, N-(2-cyanoethyl)-5-fluoro-4-fluoromethyl-4-(4-trifluoromethylphenoxy)-2-pentynamide (60 mg) was added and the mixture was heated under reflux for 1 hour. After concentrating under reduced pressure, the resulting residue was subjected to silica gel column chromatography (eluent; dichloromethane/ethyl acetate=10/1) to give the titled compound (54 mg), which was identical to the authentic sample.

Workup

  1. temperatureunder reflux
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 1 hour
  4. concentrationAfter concentrating under reduced pressure

Sources & evidence

ORD record
ord-4c73712d8dcb4adaaa8685a654fae595
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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