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N-methyl-2-pyrrolidone → 4-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinone

HRID 335451
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HRID 335451 반응식
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:22])[N:14]([CH3:21])[N:15]=[C:16]([CH3:20])[C:17]=1[S:18]C)[CH3:2].CN1CCCC1=[O:29].C[O-].[Na+]>O>[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:22])[N:14]([CH3:21])[N:15]=[C:16]([CH3:20])[C:17]=1[OH:29])[CH3:2].[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH2:10][CH3:11])[C:4]=1[C:12]1[C:13](=[O:22])[N:14]([CH3:21])[N:15]=[C:16]([CH3:20])[C:17]=1[SH:18])[CH3:2]
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참가 물질

6

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 10942334Sodium MethoxideHCID 569428794-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfanyl-2,3-dihydro-3-pyridazinone

생성물 2

HCID 546837784-(2,6-Diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-3(2H)-pyridazinoneHCID 866893584-(2,6-Diethyl-4-methylphenyl)-5-mercapto-2,6-dimethyl-2,3-dihydro-3-pyridazinone

시약·촉매·용매

1
HCID 962Water용매

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온도
90 °C

실험 절차

To a test-tube (outside diameter: 21 mm φ×overall length: 160 mm), 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-methylsulfanyl-2,3-dihydro-3-pyridazinone ((2-4)-(1)-39) (300 mg), N-methyl-2-pyrrolidone (875 mg), and sodium methoxide (410 mg) were added, and stirred at 90° C. for 16 hours. After the mixture was cooled to room temperature, water was added and washed with toluene. To the aqueous layer, 10 w/w % of hydrochloric acid was added to adjust pH to 1, and extracted with toluene 3 times. The organic layers were combined and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane:ethyl acetate=3:1) to give 185 mg of 4-(2,6-diethyl-4-methylphenyl)-5-hydroxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone ((1-4)-(1)-39) and 33 mg of 4-(2,6-diethyl-4-methylphenyl)-5-mercapto-2,6-dimethyl-2,3-dihydro-3-pyridazinone (30-a).

후처리

  1. temperatureAfter the mixture was cooled to room temperature
  2. washwashed with toluene
  3. additionTo the aqueous layer, 10 w/w % of hydrochloric acid was added
  4. extractionextracted with toluene 3 times
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-d3bf6fff03ea494f81e768515915758f
출처 데이터셋
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08884010B2

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