Water → HCID 86653068, compound

HRID 339103Notes

Reaction equation

HRID 339103 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([NH:14][CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[C:16]([F:19])([F:18])[F:17])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.[OH-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([NH:14][CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:27])([F:28])[F:29])[CH:21]=2)[C:16]([F:17])([F:18])[F:19])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86653069HCID 86653069, compound

Product 1

HCID 86653068HCID 86653068, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

626 mg (3.30 mmol) of Sn(II)Cl2 were initially charged in 5 ml of ethanol, and 350 mg (0.83 mmol) of (2E)-3-(3-nitrophenyl)-N-{2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}-acrylamide from Example 3, Stage 1 were added. The reaction solution was stirred at reflux temperature for 1 hour, cooled and admixed with 50 ml of water. While cooling with ice, the pH was adjusted to 9 with concentrated sodium hydroxide solution and the mixture was then extracted with dichloromethane. The organic phase was dried with sodium sulphate, the solvent distilled off under reduced pressure and the residue stirred with diisopropyl ether.

Workup

  1. temperatureat reflux temperature for 1 hour
  2. temperaturecooled
  3. temperatureWhile cooling with ice
  4. extractionthe mixture was then extracted with dichloromethane
  5. dry with materialThe organic phase was dried with sodium sulphate
  6. distillationthe solvent distilled off under reduced pressure
  7. stirringthe residue stirred with diisopropyl ether

Sources & evidence

ORD record
ord-dd2178ff253b41f8ae45ad4b2c2459f0
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Reaction notes

Loading…