Acetone → HCID 86675202, compound

HRID 1503023Notes

Reaction equation

HRID 1503023 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14](/[CH:16]=[CH:17]/[CH:18]([C:23]2[CH:28]=[C:27]([Cl:29])[C:26]([Cl:30])=[C:25]([Cl:31])[CH:24]=2)[C:19]([F:22])([F:21])[F:20])[CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[CH2:7][CH2:8]SC.O[O:33][S:34]([O-:36])=O.[K+].[CH3:38]C(C)=O>O>[Cl:1][C:2]1[CH:15]=[C:14](/[CH:16]=[CH:17]/[CH:18]([C:23]2[CH:24]=[C:25]([Cl:31])[C:26]([Cl:30])=[C:27]([Cl:29])[CH:28]=2)[C:19]([F:22])([F:21])[F:20])[CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6](=[O:11])[CH2:7][CH2:8][S:34]([CH3:38])(=[O:36])=[O:33]

Participants

5

Reactant 3

HCID 180AcetoneHCID 23707502Potassium hydroxy sulfiteHCID 86675203HCID 86675203, compound

Product 1

HCID 86675202HCID 86675202, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(E)-N-(2-Chloro-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzyl)-3-(methylthio)propanamide (0.15 g, 0.28 mmol) was treated with oxone (0.175 g, 0.569 mmol) in 1:1 acetone:water (20 mL) for 4 h at ambient temperature. The acetone was evaporated to obtain a white solid (0.095 g, 60%): mp 101-104° C.; 1H NMR (400 MHz, CDCl3) δ 7.41 (m, 4H), 7.24 (m, 1H), 6.53 (d, J=16.0 Hz, 1H), 6.35 (dd, J=16.0, 8.0 Hz, 1H), 6.12 (br s, 1H), 4.53 (m, 2H), 4.10 (m, 1H), 3.42 (m, 2H), 2.91 (s, 3H), 2.78 (m, 2H); ESIMS m/z 559.75 ([M−H−]).

Workup

  1. customThe acetone was evaporated

Sources & evidence

ORD record
ord-85aacfdbe57f43eda7c08aa75910a42b
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

Loading…