Hydrochloric Acid → 2-Chloro-N-ethyl-6-(1,1-dimethylethyl)benzamide

HRID 368690ノート

反応式

HRID 368690 の反応式
[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[C:7]([NH:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].CN(CCN(C)C)C.[Li]C(CC)C.[Cl:29]C(Cl)(Cl)C(Cl)(Cl)Cl.Cl>C1COCC1.C1CCCCC1.C(Cl)Cl.O>[Cl:29][C:12]1[CH:13]=[CH:14][CH:15]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:6]=1[C:7]([NH:9][CH2:10][CH3:11])=[O:8]

参加物

10

反応物 5

HCID 313Hydrochloric AcidHCID 6214HexachloroethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 186300432-tert-butyl-N-ethylbenzamideHCID 178418400CID 53628100

生成物 1

HCID 186302102-Chloro-N-ethyl-6-(1,1-dimethylethyl)benzamide

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8078Cyclohexane溶媒

反応条件

温度
-30 °C

実験手順

To a solution of 2-tert-butyl-N-ethylbenzamide (44 g, 215 mmol) and TMEDA (70 mL, 446 mmol) in 500 mL THF at -70° C. under a positive nitrogen atmosphere was added at a rapid stream 520 mL 1.3M s-BuLi in cyclohexane, maintaining the temperature at below -60° C. After the addition was complete, the resulting reaction solution was warmed to -30° C. and stirred at between -30° C. and -26° C. for 50 min. The solution was then cooled to below -70° C. and a solution of hexachloroethane (80 g) in 250 mL THF was added at between -70 and -65° C. Stirring at below -70° C. was continued for 0.5 h. The resulting reaction solution was then poured into water. CH2Cl2 and 3N HCl were added. The aq layer was separated and extracted with CH2Cl2. The combined organic layers were washed with water, dried and concentrated in vacuo. The solid was triturated with hexane and then purified by flash chromatography with 15% ethyl acetate/hexane as eluent to give the desired product as a white solid. m.p. 121-123° C.

後処理

  1. temperaturemaintaining the temperature at below -60° C
  2. additionAfter the addition
  3. customthe resulting reaction solution
  4. temperatureThe solution was then cooled to below -70° C.
  5. stirringStirring at below -70° C.
  6. waitwas continued for 0.5 h
  7. customThe resulting reaction solution
  8. customThe aq layer was separated
  9. extractionextracted with CH2Cl2
  10. washThe combined organic layers were washed with water
  11. customdried
  12. concentrationconcentrated in vacuo
  13. customThe solid was triturated with hexane
  14. custompurified by flash chromatography with 15% ethyl acetate/hexane as eluent

出典と根拠

ORDレコード
ord-b7c1152e897747faafbb455667ae8c49
出典データセット
uspto-grants-2000_10
特許番号
US06133252

反応ノート

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