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

HRID 2211168노트

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HRID 2211168 반응식
[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

참가 물질

5

반응물 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 14951339HCID 14951339, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e721b36464ef49c9852cef7ec3ba5a01
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05462952

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