Formaldehyde → 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(2,5-dihydro-2-methyl-1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazole

HRID 429268

반응식

HRID 429268 반응식
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19](=[NH:23])[N:20]([OH:22])[CH3:21])[C:3]=1[S:24]([C:26]([F:29])([F:28])[F:27])=[O:25].[CH2:30]=O>C(#N)C.C(O)(=O)C>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]2[N:20]([CH3:21])[O:22][CH2:30][N:23]=2)[C:3]=1[S:24]([C:26]([F:28])([F:29])[F:27])=[O:25]

참가 물질

5

반응물 2

HCID 712Formaldehyde2회HCID 110709345-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(N-hydroxy-N-methylamidino)-4-trifluoromethylsulfinylpyrazole

생성물 1

HCID 183547835-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(2,5-dihydro-2-methyl-1,2,4-oxadiazol-3-yl)-4-trifluoromethylsulfinylpyrazole수율 25.1%

시약·촉매·용매 2

HCID 176Acetic Acid촉매2회HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-(N-hydroxy-N-methylamidino)-4-trifluoromethylsulfinylpyrazole(1.00 g, 2.07 mmol) was dissolved in 10 ml of acetonitrile, and then aqueous 37% formaldehyde solution 840 mg (10.3 mmol) and 5 drops of acetic acid were added. After the mixture was stirred at 50° C. for 5 hours, aqueous 37% formaldehyde solution 840 mg (10.3 mmol) and, 5 drops of acetic acid were further added, followed by stirring at 50° C. for 5 hours. The reaction mixture was concentrated in vacuo and to the residual oil was added ethyl acetate, and then washed twice with an aqueous saturated sodium hydrogencarbonate solution, once with an aqueous saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the solvent was distilled off. The resulting concentrated residue was purified by silica gel column chromatography [eluent: mixed solvent of ethyl acetate and n-hexane (volume ratio=1:2)] to obtain 260 mg (0.52 mmol) of the title compound as a colorless crystal. Yield 25%.

후처리

  1. stirringby stirring at 50° C. for 5 hours
  2. concentrationThe reaction mixture was concentrated in vacuo and to the residual oil
  3. additionwas added ethyl acetate
  4. washwashed twice with an aqueous saturated sodium hydrogencarbonate solution, once with an aqueous saturated sodium chloride solution
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resulting concentrated residue was purified by silica gel column chromatography [eluent: mixed solvent of ethyl acetate and n-hexane (volume ratio=1:2)]

출처 및 근거

ORD 기록
ord-ea7655438afb498ead8192fda7830f09
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316477B1

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