Hydrazine hydrate (1:1) → HCID 54554464, 화합물

HRID 343798노트

반응식

HRID 343798 반응식
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

참가 물질

5

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 53817008HCID 53817008, 화합물

생성물 1

HCID 54554464HCID 54554464, 화합물수율 69.4%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63296f7fe705488e848402049d477ed5
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05863917

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