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

HRID 439545
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인쇄 미리보기

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HRID 439545 반응식
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]
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참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c7400e61c378451182452ad5e15faa66
출처 데이터셋
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05514719

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