Ethyl acetate hexane → 3-(Methylsulfonyl)-5-(trifluoromethyl)benzamide

HRID 623824Notes

Reaction equation

HRID 623824 reaction equation
CS[C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1)[C:6]([NH2:8])=[O:7].O[O:17][S:18]([O-:20])=O.[K+].[C:22](OCC)(=O)C.CCCCCC>CC(C)=O>[CH3:22][S:18]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=1)[C:6]([NH2:8])=[O:7])(=[O:20])=[O:17]

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 23707502Potassium hydroxy sulfiteHCID 70557756HCID 70557756, compound

Product 1

HCID 705573153-(Methylsulfonyl)-5-(trifluoromethyl)benzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 500-mL, 3-neck round-bottomed flask equipped with an 100-mL pressure-equalizing addition funnel fitted with an nitrogen inlet, and a rubber septum, 3-(methylthio)-5-(trifluoromethyl)benzamide (8.0 g, 1.0 eq.), in acetone (70 mL). Oxone (36.5 g, 2 eq.) was added at RT. The reaction was stirred for 12 h. The progress of the reaction was followed by TLC analysis on silica gel with 30% ethyl acetate-hexane as mobile phase and visualization with UV, SM Rf=0.30 and Product Rf=0.20. Reaction was stirred for 12 h and white solid (Oxone salts) was separated by filtration on a Büchner funnel and washed with acetone (100 mL). The combined acetone layer was concentrated by rotary evaporation (40° C., 20 mmHg) to afford 7.0 g of off white solid. The resulting crude compound off white (7 g) was subjected to further stage Yield (90.4%); Mass: (ES+) 267.89 (M+1).

Workup

  1. customIn a 500-mL, 3-neck round-bottomed flask equipped with an 100-mL pressure-equalizing addition funnel
  2. customfitted with an nitrogen inlet
  3. customReaction
  4. stirringwas stirred for 12 h
  5. customwhite solid (Oxone salts) was separated by filtration on a Büchner funnel
  6. washwashed with acetone (100 mL)
  7. concentrationThe combined acetone layer was concentrated by rotary evaporation (40° C., 20 mmHg)
  8. customto afford 7.0 g of off white solid
  9. customYield (90.4%)

Sources & evidence

ORD record
ord-4ee4ca2ce90d46628af6d4ba0ee9116d
Source dataset
uspto-grants-2016_04
Patent number
US09303000B2

Reaction notes

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