Water → HCID 66696626, compound

HRID 1672529Notes

Reaction equation

HRID 1672529 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH:5]=[O:6].[N+:14]([CH:16](S(C1C=CC(C)=CC=1)(=O)=O)[CH3:17])#[C-:15].C(=O)([O-])[O-].[K+].[K+].O>CO>[F:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][CH:15]=[N:14][C:16]=2[CH3:17])[CH:7]=[CH:8][C:9]=1[C:10]([F:11])([F:12])[F:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27375373-Fluoro-4-(trifluoromethyl)benzaldehydeHCID 110528851-(1-Isocyanoethanesulfonyl)-4-methylbenzene

Product 1

HCID 66696626HCID 66696626, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-fluoro-4-(trifluoromethyl)benzaldehyde (0.96 g, 5.0 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (1.05 g, 5.00 mmol), and potassium carbonate (0.898 g, 6.50 mmol) was heated to reflux for 2 hours in methanol (25 mL). After this time, the reaction mixture was cooled to room temperature and poured into water, then extracted with ether. Chromatography on silica gel (20 to 40% ethyl acetate-hexane, eluant) afforded the title compound as an off-white solid (1.01 g, 82% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.48 (s, 1H), 7.90 (m, 1H), 7.68 (m, 2H), 2.43 (s, 3H). MS (DCI+) m/z 246 (M+H), 263 (M+NH4).

Workup

  1. temperaturewas heated
  2. extractionextracted with ether

Sources & evidence

ORD record
ord-58377c899c4c43a1a65ced8f213b7a3a
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

Loading…