Toluene → HCID 86633102, compound

HRID 1012206Notes

Reaction equation

HRID 1012206 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=O)[CH3:14])=[CH:9][C:8]=1[O:16][CH3:17].[S:28]1[CH2:34][C:32](=[O:33])[NH:31][C:29]1=[S:30].C1(C)C=CC=CC=1>CCOC(C)=O>[F:1][C:2]([F:26])([F:27])[C:3]1[CH:21]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:19]=[CH:18][C:4]=1[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[C:34]2[S:28][C:29](=[S:30])[NH:31][C:32]2=[O:33])[CH3:14])=[CH:9][C:8]=1[O:16][CH3:17]

Participants

5

Reactant 3

HCID 1140Toluene2×HCID 1201546RhodanineHCID 86633101HCID 86633101, compound

Product 1

HCID 86633102HCID 86633102, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a flask with a stir bar and attached to a condenser, was added 1-[4-(2,4-Bis-trifluoromethyl-benzyloxy)-3-methoxy-phenyl]-ethanone from Step A (244 mg, 622 μmol), rhodanine (133 ng, 1.0 mmol), NH4OAc (77 mg, 1.0 mmol) and toluene (5 mL). The reaction mixture was heated to reflux and stirred for 8 h at reflux. Additional NH4OAc (50 mg) and toluene (2 mL) was added to the mixture and allowed to reflux for an additional 24 hours. The reaction solution was then diluted with EtOAc (75 mL), washed with NH4Cl (50 mL×3), dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was chromatographed (TLC, DCM/EtOAc 100:0 to 85:15) to provide the intermediate compound. (195 mg, 62% yield).

Workup

  1. customTo a flask with a stir bar and attached to a condenser
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. temperatureat reflux
  5. temperatureto reflux for an additional 24 hours
  6. washwashed with NH4Cl (50 mL×3)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude material was chromatographed (TLC, DCM/EtOAc 100:0 to 85:15)
  11. customto provide the intermediate compound

Sources & evidence

ORD record
ord-cd8bc508f2724722b59eaf7d7dbfbb73
Source dataset
uspto-grants-2011_07
Patent number
US07977489B2

Reaction notes

Loading…