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

HRID 439545
ノート
印刷プレビュー

反応式

HRID 439545 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c7400e61c378451182452ad5e15faa66
出典データセット
uspto-grants-1996_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05514719

反応ノート

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