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Acetic Anhydride → n-[4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamide

HRID 967976
ノート
印刷プレビュー

反応式

HRID 967976 の反応式
[CH3:1][C:2]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:3]=1[O:4][C:5]1[C:10]([NH2:11])=[C:9]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH:8]=[C:7]([CH3:18])[N:6]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(N(CC)CC)C>C(Cl)Cl>[CH2:14]([CH:13]([NH:12][C:9]1[CH:8]=[C:7]([CH3:18])[N:6]=[C:5]([O:4][C:3]2[C:19]([CH3:24])=[CH:20][C:21]([CH3:23])=[CH:22][C:2]=2[CH3:1])[C:10]=1[NH:11][C:25](=[O:27])[CH3:26])[CH2:16][CH3:17])[CH3:15]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 219121512-(2,4,6-trimethylphenoxy)-N4-(1-ethylpropyl)-6-methyl-pyridine-3,4-diamine

生成物 1

HCID 53966610n-[4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamide収率 89%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 2-(2,4,6-trimethyl-phenoxy)-N4-(1-ethyl-propyl)-6-methyl-pyridine-3,4-diamine (250 mg, 0.763 mmol), acetic anhydride (72 mg, 0.763 mmol) and triethylamine (77 mg, 0.763 mmol) in 5 ml of methylene chloride was stirred at room temperature for 3 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to dryness to give 310 mg of the crude material. The crude material was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give 250 mg (89% yield) of N-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamide as tan solid, mp 154-156° C. 1H NMR (CDCl3) δ 6.97 (0.64H), 6.86 (s, 2H), 6.26 (0.36H), 6.14 (0.64H), 6.12 (s, 0.36H), 4.80 (d, 0.64H), 4.40 (d, 0.36H), 3.2-3.4 (m, 1H), 2.29 (s, 3H), 2.26 (s, 1.9H), 2.17 (s, 1.1H), 2.16 (s, 1.9H), 2.06 (s, 6H), 1.99 (s, 1.1H), 1.4-1.75 (m, 4H), 0.97 (t, 6H) ppm.

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated to dryness
  5. customto give 310 mg of the crude material
  6. customThe crude material was purified through silica gel column chromatography

出典と根拠

ORDレコード
ord-fd78d3ebae30462ca5086e6e9daecc59
出典データセット
uspto-grants-2005_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06956047B1

反応ノート

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