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Potassium Carbonate → 3,5-dimethyl-benzoic acid N'-(2-allyloxymethyl-3-methyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazide

HRID 1774024
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HRID 1774024 반응식
[C:1]([NH:5][NH:6][C:7](=[O:21])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH3:15])[C:9]=1[CH2:16][O:17][CH2:18][CH:19]=[CH2:20])([CH3:4])([CH3:3])[CH3:2].[CH3:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([CH3:32])[CH:31]=1)[C:26](Cl)=[O:27].[C:33]([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.O>[CH2:18]([O:17][CH2:16][CH:9]1[C:10]([CH3:33])([O:14][CH3:15])[CH:11]=[CH:12][CH:13]=[C:8]1[C:7]([NH:6][N:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:26](=[O:27])[C:25]1[CH:24]=[C:23]([CH3:22])[CH:31]=[C:30]([CH3:32])[CH:29]=1)=[O:21])[CH:19]=[CH2:20]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 810883,5-Dimethylbenzoyl ChlorideHCID 598385982-allyloxymethyl-3-methoxy-benzoic acid N'-tert-butyl-hydrazide

생성물 1

HCID 866766673,5-dimethyl-benzoic acid N'-(2-allyloxymethyl-3-methyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazide수율 80.1%

시약·촉매·용매 2

HCID 962Water용매
HCID 6344Dichloromethane용매2회

실험 절차

To a flask containing 2.0 g (0.0068 mol) of 2-allyloxymethyl-3-methoxy-benzoic acid N′-tert-butyl-hydrazide dissolved in 15 mL of CH2Cl2 was added 1.27 g (0.0075 mol) of 3,5-dimethylbenzoyl chloride in 10 mL of CH2Cl2 and 2.84 g of K2CO3 (0.02 mol) in 30 mL of H2O. The mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted and partitioned, and the organic phase was dried and solvent was removed in vacuo. The product was purified by silica gel chromatography; eluting in 25% ethyl acetate:hexane fractions, to yield 2.40 g of pure 3,5-dimethyl-benzoic acid N′-(2-allyloxymethyl-3-methyl-3-methoxy-benzoyl)-N-tert-butyl-hydrazide. 1H NMR (CDCl3, 300 MHz) δ (ppm): 7.2 (t, 1H,) 7.1 (s, 1H), 7.05 (d, 2H), 6.95 (m, 2H), 5.9 (m, 1H), 5.2-5.3 (q, 2H), 4.5 (d, 2H), 3.9 (m, 2H), 3.80 (s, 3H), 2.245 (s, 6H), 1.54 7 (s, 9H).

후처리

  1. additionThe reaction mixture was diluted
  2. custompartitioned
  3. customthe organic phase was dried
  4. customsolvent was removed in vacuo
  5. customThe product was purified by silica gel chromatography
  6. washeluting in 25% ethyl acetate

출처 및 근거

ORD 기록
ord-c9b7fe01e94d48c1a975fe4e06bf6a93
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09255273B2

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