Methanol → Methyl 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoate

HRID 467932노트

반응식

HRID 467932 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.S(Cl)(Cl)=O.[CH3:32]O>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:32][O:19][C:18](=[O:20])[C:17]1[CH:21]=[CH:22][C:14]([C:11]2[CH2:10][C:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)([C:24]([F:25])([F:27])[F:26])[O:13][N:12]=2)=[CH:15][C:16]=1[CH3:23]

참가 물질

6

반응물 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 231598114-(5-(3,5-Dichlorophenyl)-5-(tri fluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoic acid

생성물 1

HCID 59563501Methyl 4-(5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzoate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

To a suspension 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid (Example I5) (10 g) in toluene (150 ml) and dimethylformamide (0.1 ml) at ambient temperature was added dropwise thionyl chloride (3.5 ml). The reaction mixture was stirred at 50° C. for 2 hours. The solution was then cooled to 0° C. and methanol (2 ml) added slowly. The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was concentrated and aqueous sodium hydrogen carbonate (saturated) (50 ml) added to the residue. The mixture was extracted with ethyl acetate (3×100 ml). The combined organic extracts were dried over sodium sulfate and concentrated to afford 4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-benzoic acid methyl ester as a yellow solid (11.5 g). 1H-NMR (CDCl3, 400 MHz): 7.95 (d, 1H), 7.55 (m, 4H), 7.45 (s, 1H), 4.10 (d, 1H), 3.90 (s, 3H), 3.70 (d, 1H), 2.60 (s, 3H) ppm.

후처리

  1. customat ambient temperature
  2. temperatureThe solution was then cooled to 0° C.
  3. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  4. concentrationThe reaction mixture was concentrated
  5. additionaqueous sodium hydrogen carbonate (saturated) (50 ml) added to the residue
  6. extractionThe mixture was extracted with ethyl acetate (3×100 ml)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d3de05240e99441e92f785444499927a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623896B2

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