Sodium Hydroxide → HCID 11652360, compound

HRID 1014071Notes

Reaction equation

HRID 1014071 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[S:8])=[CH:5][CH:4]=1.Cl[CH:15]([C:20]([CH3:22])=O)[C:16]([O:18][CH3:19])=[O:17].[OH-].[Na+]>O1CCCC1>[CH3:22][C:20]1[N:9]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([C:2]([F:1])([F:12])[F:13])=[CH:4][CH:5]=2)[S:8][C:15]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 107332Methyl 2-chloroacetoacetateHCID 27348234-(Trifluoromethyl)thiobenzamide

Product 1

HCID 11652360HCID 11652360, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
77.5 °C

Procedure

4-(Trifluoromethyl)thiobenzamide (20.5 g, 0.1 mol) was dissolved in tetrahydrofuran (300 ml) at room temperature, and then methyl 2-chloroacetoacetate (12.2 ml, 0.1 mol, 1.0 eq.) was added slowly for about 20 minutes therein while stirring. After completion of addition, the mixture was stirred again at room temperature for 30 minutes, and then the mixture was heated and refluxed at 75 to 80° C. for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature. Subsequently, 50% aqueous solution of sodium hydroxide (150 ml) was added and stirred for 20 minutes. The resultant organic layer was separated by extraction with brine and ethyl acetate, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to thereby yield 28.8 g of the title compound (yield: 95.6%).

Workup

  1. additionAfter completion of addition
  2. stirringthe mixture was stirred again at room temperature for 30 minutes
  3. temperaturethe mixture was heated
  4. customAfter completion of the reaction
  5. temperaturethe reaction mixture was cooled to room temperature
  6. stirringstirred for 20 minutes
  7. customThe resultant organic layer was separated by extraction with brine and ethyl acetate
  8. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-3bcd5e2d2ff8443d839076c8de601314
Source dataset
uspto-grants-2011_07
Patent number
US07982050B2

Reaction notes

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