1,2-Dichloroethane → N,N-diethyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamide

HRID 439545Notes

Reaction equation

HRID 439545 reaction equation
ClCCCl.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15]2[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:16]=2[C:17](O)=[O:18])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].S(Cl)(Cl)=O.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33]>O1CCCC1.CN(C)C=O>[CH2:32]([N:34]([CH2:35][CH3:36])[C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:15]=1[C:9]1[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH3:5])[CH:8]=1)[CH3:33]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 157662622-(3,4-Dimethoxyphenyl)-4-(trifluoromethyl)benzoic acid

Product 1

HCID 11068964N,N-diethyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamideYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

500 ml of 1,2-dichloroethane, 60 g (0.184 mol) of 2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzoic acid and 5 ml of N,N-dimethylformamide are introduced successively into a 1000 ml round-bottomed flask. 20 ml of thionyl chloride (0.276 mol) are then run in dropwise with stirring and while cooling at 0° C. When the addition is finished, the reaction mixture is heated progressively to 55° C. over 2 hours and then evaporated to dryness. The residue is taken up in 200 ml of tetrahydrofuran and then poured dropwise into a solution containing 58 ml (0.55 mol) of diethylamine in 200 ml of tetrahydrofuran maintained at a temperature below 10° C. When the addition is finished, the reaction mixture is stirred at room temperature for one hour and then evaporated to dryness. The residue is taken up in dichloromethane and washed successively with 1N HCl and distilled water. After drying over magnesium sulfate, the organic phase is evaporated under reduced pressure to provide 62.3 g (yield: 89%) of N,N-diethyl-2-(3,4-dimethoxyphenyl)-4-(trifluoromethyl)benzamide in the form of a white solid melting at 109°-110° C.

Workup

  1. additionWhen the addition
  2. temperaturethe reaction mixture is heated progressively to 55° C. over 2 hours
  3. customevaporated to dryness
  4. additionpoured dropwise into a solution
  5. temperaturemaintained at a temperature below 10° C
  6. additionWhen the addition
  7. stirringthe reaction mixture is stirred at room temperature for one hour
  8. customevaporated to dryness
  9. washwashed successively with 1N HCl
  10. distillationdistilled water
  11. dry with materialAfter drying over magnesium sulfate
  12. customthe organic phase is evaporated under reduced pressure

Sources & evidence

ORD record
ord-c7400e61c378451182452ad5e15faa66
Source dataset
uspto-grants-1996_05
Patent number
US05514719

Reaction notes

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