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

HRID 25946

반응식

HRID 25946 반응식
[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

참가 물질

9

반응물 4

HCID 1060Pyruvic AcidHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 213256842',5-dichloro-3-(3-aminomethyl-5-methyl-4H-1,2,4-triazol-4-yl)-benzophenone dihydrobromide

생성물 1

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

시약·촉매·용매 4

HCID 241Benzene용매HCID 6212Chloroform용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9ffa1233d3a54301a7b399e8045faf43
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04147700

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