Isonicotinic Acid → 5'-Chloro-2'-phenoxyisonicotinanilide

HRID 27632

反応式

HRID 27632 の反応式
S(Cl)(Cl)=O.[C:5]([OH:13])(=O)[C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([CH:21]=1)[NH2:20].[OH-].[Na+]>O1CCCC1.C(N(CC)CC)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([CH:21]=1)[NH:20][C:5](=[O:13])[C:6]1[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=1

参加物

7

反応物 4

HCID 5922Isonicotinic AcidHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 667385-Chloro-2-phenoxyaniline

生成物 1

HCID 48256825'-Chloro-2'-phenoxyisonicotinanilide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

A 100 ml. portion of thionyl chloride is added dropwise to 28.0 g. of isonicotinic acid over 30 minutes. After an additional 30 minutes the mixture becomes honogeneous. The volatiles are removed in vacuo, 250 ml. of benzene is added and then removed to leave a residue. This residue is suspended in 300 ml of dry tetrahydrofuran and a solution of 25.0 g. of 5-chloro-2-phenoxyaniline in 63 ml. of triethylamine is added dropwise over 30 minutes and the mixture is stirred overnight. The mixture is poured into 500 ml. of 1 N-sodium hydroxide. The organic layer is separated. The basic layer is extracted with two 100 ml. portions of ether. The ether extracts and organic layer are combined, washed with 250 ml. of water and then with four 200 ml. portions of 10% hydrochloric acid. The combined acid washings are neutralized with concentrated ammonium hydroxide and extracted with three 250 ml. portions of ether. These ether extracts are dried and evaporated giving 5'-chloro2'-phenoxy-isonicotinanilide as a brown solid.

後処理

  1. customThe volatiles are removed in vacuo, 250 ml
  2. additionof benzene is added
  3. customremoved
  4. customto leave a residue
  5. additionThe mixture is poured into 500 ml
  6. customThe organic layer is separated
  7. extractionThe basic layer is extracted with two 100 ml
  8. washwashed with 250 ml
  9. extractionextracted with three 250 ml
  10. dry with materialThese ether extracts are dried
  11. customevaporated

出典と根拠

ORDレコード
ord-0cba76c30a56460d80a09a6e276bb90a
出典データセット
uspto-grants-1980_09
特許番号
US04221715

関連ノート

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