Hydrazine hydrate (1:1) → HCID 54554464、化合物

HRID 343798ノート

反応式

HRID 343798 の反応式
O.NN.[Cl:4][C:5]1[C:6]([N:20]([CH2:25][CH2:26][N:27]2C(=O)C3=CC=CC=C3C2=O)[S:21]([CH3:24])(=[O:23])=[O:22])=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11]=[C:10]([O:16][CH3:17])[C:9]([O:18][CH3:19])=[N:8]2>ClCCl.CO>[Cl:4][C:5]1[C:6]([N:20]([CH2:25][CH2:26][NH2:27])[S:21]([CH3:24])(=[O:23])=[O:22])=[C:7]2[C:12](=[CH:13][C:14]=1[Cl:15])[N:11]=[C:10]([O:16][CH3:17])[C:9]([O:18][CH3:19])=[N:8]2

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 53817008HCID 53817008、化合物

生成物 1

HCID 54554464HCID 54554464、化合物収率 69.4%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

Hydrazine hydrate (696 μl, 716 mg, 14.3 mmol) was added dropwise to a solution of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-phthalimidoethyl)methanesulphonamide (3.76 g, 7.15 mmol) in a mixture of dichloromethane (71 ml) and methanol (5 ml) at room temperature under nitrogen. The mixture was heated at reflux for 4 days and then further methanol (20 ml) was added. After a further 2 days the mixture was allowed to cool and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and this was extracted 3 times with 10% aqueous citric acid. The combined acid extracts were adjusted to pH 9 with solid potassium carbonate and extracted 3 times with dichloromethane. The combined dichloromethane extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with 95:5 dichloromethane:methanol to give N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-N-(2-aminoethyl)methanesulphonamide (1.96 g, 69%) as a pale yellow solid.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 days
  3. temperatureto cool
  4. concentrationwas concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. extractionthis was extracted 3 times with 10% aqueous citric acid
  7. extractionextracted 3 times with dichloromethane
  8. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography on silica gel eluting with 95:5 dichloromethane

出典と根拠

ORDレコード
ord-63296f7fe705488e848402049d477ed5
出典データセット
uspto-grants-1999_01
特許番号
US05863917

反応ノート

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