2-Methoxy-5-nitropyridine → 6-Methoxy-3-nitro-2-(toluene-4-sulfonylmethyl)-pyridine

HRID 497414

反応式

HRID 497414 の反応式
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.Cl[CH2:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15].CC(C)([O-])C.[K+]>CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=2)(=[O:15])=[O:16])[C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 795252-Methoxy-5-nitropyridineHCID 5628451-Chloromethanesulfonyl-4-methylbenzeneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 136265146-Methoxy-3-nitro-2-(toluene-4-sulfonylmethyl)-pyridine収率 37.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 15.4 g (0.1 mol) of 6-methoxy-3-nitropyridine and 20.4 g (0.1 mol) of 1-chloromethane-sulfonyl-4-methyl-benzene is dissolved in 100 mL of DMF and cooled to 5 C. To this solution is added, dropwise, 100 mL (0.1 mol) of a 1M solution of potassium t-butoxide in THF, keeping the temperature ≦10 C. The dark reaction mixture is stirred for 18 hours at room temperature. The reaction mixture is evaporated to remove the THF, and to the remaining solution is added 100 mL of water. A dark brown precipitate formed which is collected by filtration. This solid is triturated with isopropyl ether for 1 hour and refiltered to yield 12 grams of 6-methoxy-3-nitro-2-(toluene-4-sulfonylmethyl)-pyridine. 1H NMR (CDCl3) δ 8.25 (d, 1H), 7.60 (m, 2H), 7.30 (m, 2H), 6.80 (d, 1H), 5.10 (s, 1H), 3.75 (s, 3H), 2.40 (s, 3H). Mass Spectrum: m/e=323.1 (p+1), TLC (CDCl3) Rf=0.45 Step 2:

後処理

  1. temperaturecooled to 5 C
  2. additionTo this solution is added
  3. customThe dark reaction mixture
  4. customThe reaction mixture is evaporated
  5. customto remove the THF
  6. additionto the remaining solution is added 100 mL of water
  7. customA dark brown precipitate formed which
  8. filtrationis collected by filtration
  9. customThis solid is triturated with isopropyl ether for 1 hour

出典と根拠

ORDレコード
ord-ee4fbb90b9de42b094f980cd6699cdcf
出典データセット
uspto-grants-2005_09
特許番号
US06949562B2

関連ノート

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