1,1-Dimethylhydrazine → HCID 18696625、化合物

HRID 1870555ノート

反応式

HRID 1870555 の反応式
[N:1]([C:4]1[C:5]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)=[C:2]=[O:3].C[N:25]([CH3:27])[NH2:26].[Cl:28][C:29](Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O1CCCC1.C(Cl)Cl>[Cl:28][C:29]1[N:1]([C:4]2[C:5]([O:10][C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:12]=3)=[N:6][CH:7]=[CH:8][CH:9]=2)[C:2](=[O:3])[N:25]([CH3:27])[N:26]=1

参加物

6

反応物 3

HCID 59761,1-DimethylhydrazineHCID 94429TriphosgeneHCID 186966243-Isocyanato-2-(3-phenoxyphenoxy)pyridine

生成物 1

HCID 18696625HCID 18696625、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

The solids from Step B were dissolved in 100 mL of dry tetrahydrofuran. 1,1-Dimethylhydrazine (3 g, 50.0 mmol) was added and the reaction mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and extracted twice with diethyl ether. The combined organic layers were then washed once with saturated aqueous NaCl solution and dried over magnesium sulfate. The solvent was removed under reduced pressure to give an oil. This oil was then dissolved in 200 mL methylene chloride and cooled to 0° C. at which temperature triphosgene (4.08 g, 13.7 mmol) was added. The reaction mixture was refluxed for 16 h, cooled to room temperature and washed once with water. The organic layer was then dried over magnesium sulfate and concentrated under reduced pressure to yield a crude oil which was purified by silica gel chromatography using 3:2/hexanes:ethyl acetate as the eluent to yield 2 g of the title compound of Step C, a compound of the invention, as a solid. 1H NMR (CDCl3 ; 300 MHz): δ 3.53 (s,3H), 6.8-6.9 (m,3H), 7.0-7.2 (m,4H), 7.3-7.4 (m,3H), 7.71 (dd,1H, J=1.9, 7.7 Hz), 8.27 (dd,1H, J=1.8, 4.9 Hz).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted twice with diethyl ether
  4. washThe combined organic layers were then washed once with saturated aqueous NaCl solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto give an oil
  8. additionwas added
  9. temperatureThe reaction mixture was refluxed for 16 h
  10. temperaturecooled to room temperature
  11. washwashed once with water
  12. dry with materialThe organic layer was then dried over magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customto yield a crude oil which
  15. customwas purified by silica gel chromatography

出典と根拠

ORDレコード
ord-19b46df86edf4634bd8976bf26fd6351
出典データセット
uspto-grants-2000_08
特許番号
US06096895

反応ノート

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