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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
ノート
印刷プレビュー

反応式

HRID 1774024 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒
2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c9b7fe01e94d48c1a975fe4e06bf6a93
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09255273B2

反応ノート

読み込み中…

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