Hydrochloric Acid → HCID 86742629、化合物

HRID 414662

反応式

HRID 414662 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[Na].Cl[C:15]1[CH:16]=[C:17]([C:22]([F:25])([F:24])[F:23])[CH:18]=[CH:19][C:20]=1Cl.[ClH:26]>CS(C)=O.[Cu]>[Cl:26][C:18]1[CH:19]=[C:20]([O:12][C:10]2[CH:11]=[C:4]([OH:3])[C:5](=[CH:8][CH:9]=2)[C:6]#[N:7])[CH:15]=[CH:16][C:17]=1[C:22]([F:25])([F:24])[F:23]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 94813,4-DichlorobenzotrifluorideHCID 24758Sodium hydrideHCID 30175202,4-DihydroxybenzonitrileHCID 5360545Sodium

生成物 1

HCID 86742629HCID 86742629、化合物

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 679Dimethyl Sulfoxide溶媒2 回

反応条件

温度
115 °C

実験手順

To a suspension of 19.2 g of sodium hydride in 400 ml of dimethyl sulphoxide is added dropwise a solution of 54.0 g of 2,4-dihydroxybenzonitrile in 200 ml of dimethyl sulphoxide. After formation of the sodium salt 86.0 g of 3,4-dichloro-α,α,α-trifluorotoluene and 0.1 g of copper powder are added and the reaction mixture is stirred at 115° C. for 68 hours. Then the mixture is poured onto 2 kg of ice and the aqueous mixture acidified with concentrated hydrochloric acid and extracted severl times with 500 ml portions of ethyl acetate. The combined organic phases are neutralized and dried over anhydrous sodium sulphate, and the solvent is evaporated off under reduced pressure. Finally, the residue is prified by column chromatographyon silica gel using ethyl acetate / n-hexane (7:3) as the eluent and crystallized from methylene chloride. There is obtained the intermediate 4-[(2-chloro-α,α,α-trifluoro-p-tolyl)oxy]-salicylonitrile, m.p. 155°-156° C.; mass spectrum; m/e 313, 294, 278, 250,223, 209, 90, 63; infrared spectrum: main peak at 2230 cm-1.

後処理

  1. extractionextracted severl times with 500 ml portions of ethyl acetate
  2. dry with materialdried over anhydrous sodium sulphate
  3. customthe solvent is evaporated off under reduced pressure
  4. customcrystallized from methylene chloride

出典と根拠

ORDレコード
ord-26844c7f84814b4eab0fb341676c0f7a
出典データセット
uspto-grants-1988_12
特許番号
US04792616

関連ノート

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