HCID 20112055, compound → HCID 86675213, compound

HRID 1503033Notes

Reaction equation

HRID 1503033 reaction equation
B([O-])([O-])[O-].[Si+4].B([O-])([O-])[O-].B([O-])([O-])[O-].B([O-])([O-])[O-].[Si+4].[Si+4].[F:20][C:21]([F:50])([F:49])[CH2:22][C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[CH:35]([C:40]2[CH:45]=[C:44]([Cl:46])[C:43]([Cl:47])=[C:42]([Cl:48])[CH:41]=2)[C:36]([F:39])([F:38])[F:37])=[CH:29][CH:28]=1)=[O:24]>CS(C)=O>[F:49][C:21]([F:20])([F:50])[CH2:22][C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]\[CH:35]([C:40]2[CH:41]=[C:42]([Cl:48])[C:43]([Cl:47])=[C:44]([Cl:46])[CH:45]=2)[C:36]([F:37])([F:38])[F:39])=[CH:29][CH:28]=1)=[O:24]

Participants

4

Reactant 2

HCID 20112055HCID 20112055, compoundHCID 86675214HCID 86675214, compound

Product 1

HCID 86675213HCID 86675213, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A silicon borate vial was charged with (E)-3,3,3-trifluoro-N-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzyl)propanamide (133 mg, 0.269 mmol) and dimethyl sulfoxide (DMSO; 10 mL). The mixture was placed within 0.6 to 1 meter (m) of a bank of eight 115 watt Sylvania FR48T12/350BL/VHO/180 Fluorescent Tube Black Lights and four 115 watt Sylvania (daylight) F48T12/D/VHO Straight T12 Fluorescent Tube Lights for 72 h. The mixture was concentrated in vacuo and purified by reverse phase chromatography to give the title compound as a colorless oil (11 mg, 8%): 1H NMR (300 MHz, CDCl3) δ 7.28 (s, 2H), 7.25 (m, 2H), 7.10 (d, J=8.0 Hz, 2H), 6.89 (d, J=11.4 Hz, 1H), 6.07 (br s, 1H), 6.01 (m, 1H), 4.51 (d, J=5.8 Hz, 2H), 4.34 (m, 1H), 3.12 (q, J=7.5 Hz, 2H); 13C NMR (101 MHz, CDCl3) δ 162.44, 137.20, 135.38, 135.23, 134.82, 134.68, 131.71, 129.00, 128.80, 128.69, 128.10, 127.96, 122.63, 76.70, 47.33 (q, J=28 Hz), 43.59, 42.12 (q, J=30 Hz); ESIMS m/z 504 ([M+H]+).

Workup

  1. customfor 72 h
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-6cb2c2281f36422490dd6b0d967333b9
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

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