Carbon Disulfide → 5-[2-(2,6-Dichloro-3-methyl-phenylamino)-phenyl]-[1,3,4]oxadiazole-2-thiol

HRID 2211168ノート

反応式

HRID 2211168 の反応式
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH:15][NH2:16])=[O:14].[C:21](=S)=[S:22].[OH-].[K+]>CO>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]1[O:14][C:21](=[S:22])[NH:16][N:15]=1

参加物

5

反応物 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 14951339HCID 14951339、化合物

生成物 1

HCID 99284195-[2-(2,6-Dichloro-3-methyl-phenylamino)-phenyl]-[1,3,4]oxadiazole-2-thiol収率 65%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

2-[(2,6-Dichloro-3-methylphenyl)amino]-benzoic acid, hydrazide (1.172 g, 3.78 mmol) is dissolved in 20 ml of methanol, and the solution is cooled to 0° C. Carbon disulfide (520 μl, 8.82 mmol) is added, followed by potassium hydroxide (266.0 mg, 4.03 mmol). The solution is heated at reflux for seven hours and allowed to cool to room temperature overnight. The solution is concentrated in vacuo and the residue dissolved in water. The aqueous solution is acidified with 1N hydrochloric acid and the resulting solids extracted into a 1:1 mixture of ether and ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is chromatographed, eluting with hexane:ethyl acetate (2:1) providing 864.0 mg (65%) of product, mp 257°-259° C.

後処理

  1. temperatureThe solution is heated
  2. temperatureat reflux for seven hours
  3. temperatureto cool to room temperature overnight
  4. concentrationThe solution is concentrated in vacuo
  5. dissolutionthe residue dissolved in water
  6. extractionthe resulting solids extracted into a 1:1 mixture of ether and ethyl acetate
  7. dry with materialThe organic layer is dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is chromatographed
  11. washeluting with hexane:ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-e721b36464ef49c9852cef7ec3ba5a01
出典データセット
uspto-grants-1995_10
特許番号
US05462952

反応ノート

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