丙酮酸 → 2',5-dichloro-3-(3-pyruvamidomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone

HRID 25946

反应方程式

HRID 25946 反应方程式
[C:1]([OH:6])(=O)[C:2]([CH3:4])=[O:3].S(Cl)(Cl)=O.Br.Br.[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:36])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([N:28]2[C:32]([CH3:33])=[N:31][N:30]=[C:29]2[CH2:34][NH2:35])[CH:22]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.CN(C)C=O.C1C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:36])[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([N:28]2[C:32]([CH3:33])=[N:31][N:30]=[C:29]2[CH2:34][NH:35][C:1](=[O:6])[C:2]([CH3:4])=[O:3])[CH:22]=1

参与物

9

反应物 4

HCID 1060丙酮酸HCID 24386氯化亚砜HCID 516892碳酸氢钠HCID 213256842',5-dichloro-3-(3-aminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone dihydrobromide

产物 1

HCID 213257442',5-dichloro-3-(3-pyruvamidomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone收率 64.8%

试剂、催化剂与溶剂 4

HCID 241苯溶剂HCID 6212三氯甲烷溶剂HCID 6228N,N-二甲基甲酰胺溶剂HCID 8857乙酸乙酯溶剂

实验过程

A solution of pyruvic acid (0.33 g) and thionyl chloride (0.27 g) in chloroform (2 ml) is refluxed for 1 hour. After cooling, the solution is mixed with 2',5-dichloro-3-(3-aminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone dihydrobromide (1.31 g), benzene (6 ml) and dimethylformamide (11 ml) at 0° C. The resultant mixture is stirred at room temperature for 3 hours and allowed to stand overnight. The reaction mixture is neutralized with aqueous sodium bicarbonate and shaken with ethyl acetate. The organic layer is washed with water, dried and evaporated to remove the solvent. The residue is recrystallized from ethyl acetate to give 2',5-dichloro-3-(3-pyruvamidomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone (0.7 g) as crystals melting at 178° to 180° C.

后处理

  1. temperatureAfter cooling
  2. washThe organic layer is washed with water
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is recrystallized from ethyl acetate

来源与证据

ORD记录
ord-9ffa1233d3a54301a7b399e8045faf43
来源数据集
uspto-grants-1979_04
专利号
US04147700

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