Sulfuric Acid → 1-(2,4-dichloro-phenyl)-4-methyl-5-(4-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid

HRID 526710

반응식

HRID 526710 반응식
C([O:3][C:4]([C:6](=O)[CH:7]([CH3:20])[CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1)[O-])=[O:5])C.[Li+].Cl.[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[NH:32][NH2:33].S(=O)(=O)(O)O>C(O)C>[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[N:32]1[C:8]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:14][CH:15]=2)=[C:7]([CH3:20])[C:6]([C:4]([OH:3])=[O:5])=[N:33]1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 2723905(2,4-Dichlorophenyl)hydrazine monohydrochlorideHCID 89907367Lithium 3-ethoxycarbonyl-2-methyl-3-oxo-1-(4-trifluoromethyl-phenyl)-propan-1-olate

생성물 1

HCID 441917461-(2,4-dichloro-phenyl)-4-methyl-5-(4-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 10 g of Lithium 3-ethoxycarbonyl-2-methyl-3-oxo-1-(4-trifluoromethyl-phenyl)-propan-1-olate, 6.9 g of (2,4-Dichloro-phenyl)-hydrazine hydrochloride and 74 ml of sulfuric acid (50%) in 184 ml of ethanol was heated to reflux for 7 h. After cooling to room temperature the organic solvents were removed under reduced pressure and the residue was diluted with 100 ml of water and extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and the solvent was removed under reduced pressure. The residue was dissolved in 100 ml THF and a solution of 1.4 g of LiOH in 20 ml water was added at room temperature. The reaction mixture was heated to 60° C. for 7 h. Then, after cooling to room temperature the mixture was acidified to pH 1 by addition of half-concentrated hydrochloric acid.

후처리

  1. temperatureto reflux for 7 h
  2. customwere removed under reduced pressure
  3. additionthe residue was diluted with 100 ml of water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customthe solvent was removed under reduced pressure
  7. dissolutionThe residue was dissolved in 100 ml THF
  8. additiona solution of 1.4 g of LiOH in 20 ml water was added at room temperature
  9. temperatureThe reaction mixture was heated to 60° C. for 7 h
  10. temperatureThen, after cooling to room temperature the mixture
  11. additionwas acidified to pH 1 by addition of half-concentrated hydrochloric acid

출처 및 근거

ORD 기록
ord-9cbc4f754a144a7da6ce96856005e523
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346762B2

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