Benzene → 3-(4,5-Dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride

HRID 1857319노트

반응식

HRID 1857319 반응식
[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=2[S:15]([CH3:18])(=[O:17])=[O:16])[C:9](O)=[O:10])=[N:2]1.C1C=CC=CC=1.S(Cl)([Cl:28])=O>N1C=CC=CC=1>[O:1]1[CH2:5][CH2:4][C:3]([C:6]2[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=2[S:15]([CH3:18])(=[O:17])=[O:16])[C:9]([Cl:28])=[O:10])=[N:2]1

참가 물질

5

반응물 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 154774763-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)benzoic acid

생성물 1

HCID 112550833-(4,5-Dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To 2.75 g of 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoic acid were added 30 ml of benzene, then 1.7 ml of thionyl chloride and a drop of pyridine to heat at reflux for 3 hours. The reaction solution was cooled down. The solvent was distilled out under reduced pressure to give 2.90 g of 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride. Separately 0.93 g of 1-ethyl-5-hydroxypyrazole hydrochloride was dissolved in 20 ml of chloroform, and 1.60 g of triethylamine was added, while cooling with ice. Into the obtained solution was added dropwise 10 ml of a chloroform solution containing 1.90 g of 3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-2-methylbenzoyl chloride to stir at room temperature for 30 minutes, and 0.76 g of triethylamine and 0.16 g of acetone cyanohydrin were added to further stir overnight. The reaction solution was washed with dilute hydrochloric acid, then with a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled out under reduced pressure. Methanol was added to the residue. The obtained crystals were separated by filtration to give 1.59 g of the title compound as white crystals. m.p. 183~184.5° C.

후처리

  1. temperatureat reflux for 3 hours
  2. temperatureThe reaction solution was cooled down
  3. distillationThe solvent was distilled out under reduced pressure

출처 및 근거

ORD 기록
ord-85a53e5f13014b5d9215b35fa6e6a1f1
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147031

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