Ammonia → HCID 178512013、化合物

HRID 1025662ノート

反応式

HRID 1025662 の反応式
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=O.P(Cl)(Cl)(Cl)(Cl)Cl.[NH3:28].C([O-])(O)=O.[Na+]>C1C=CC=CC=1.C1COCC1.C(OC(=O)C)C>[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)=[NH:28]

参加物

8

反応物 4

HCID 222AmmoniaHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 9564532,4-dichloro-N-(4-(trifluoromethyl)phenyl)benzamide

生成物 1

HCID 178512013HCID 178512013、化合物収率 89%

試薬・触媒・溶媒 3

HCID 241Benzene溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

Part B: 2,4-Dichloro-N-(4-(trifluoromethyl)phenyl)benzamide (19.0 g, 0.057 mol) is dissolved in benzene (150 mL) and PCl5 (13.0 g, 1.1 molar equivalent) is added. The resulting mixture is heated at reflux temperature for two hours, allowed to attain room temperature and concentrated in vacuo to give a residue. The residue is dissolved in anhydrous THF, cooled to 0° C. and transferred into an autoclave. Excess NH3 is quickly added from a lecture bottle and the mixture is stirred at room temperature for 50 hours. A mixture of ethylacetate and aqueous NaHCO3 is added. The ethylacetate layer is collected, dried over Na2SO4, filtered and concentrated in vacuo. The resulting oil is purified by column chromatography (diethyl ether/petroleum ether=1/1 (v/v), silicagel) to give pure 2,4-dichloro-N-(4-(trifluoromethyl)phenyl)benzene-carboxamidine (16.9 g, 89% yield). Melting point: 108-109° C.

後処理

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux temperature for two hours
  3. customto attain room temperature
  4. concentrationconcentrated in vacuo
  5. customto give a residue
  6. additionis added
  7. customThe ethylacetate layer is collected
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe resulting oil is purified by column chromatography (diethyl ether/petroleum ether=1/1 (v/v), silicagel)

出典と根拠

ORDレコード
ord-cd3909ae8c4c42849ce9afeb6e1042de
出典データセット
uspto-grants-2014_05
特許番号
US08729101B2

反応ノート

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