Water → N1-Benzyl-N2-(6-chloro-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine

HRID 2093361노트

반응식

HRID 2093361 반응식
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[C:6]([CH3:9])[C:7]=1[CH3:8].[CH2:11]([NH:18][CH2:19][CH2:20][NH2:21])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[CH2:11]([NH:18][CH2:19][CH2:20][NH:21][C:5]1[N:4]=[N:3][C:2]([Cl:1])=[C:7]([CH3:8])[C:6]=1[CH3:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 77801N-BenzylethylenediamineHCID 81531DiisopropylethylamineHCID 211875053,6-Dichloro-4,5-dimethylpyridazine

생성물 1

HCID 86655911N1-Benzyl-N2-(6-chloro-4,5-dimethylpyridazin-3-yl)ethane-1,2-diamine

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

Heat a mixture of 3,6-dichloro-4,5-dimethylpyridazine (6.90 g, 39.0 mmol), N-benzylethylenediamine (8.78 g, 58.5 mmol), and diisopropylethylamine (25.2 g, 195 mmol) in DMSO (78 mL) at 120° C. for 3 d. Cool the reaction mixture, pour into H2O, and extract the mixture with Et2O. Wash the organic layer with H2O, dry over Na2SO4, filter, and concentrate under reduced pressure. Purify the residue using flash silica gel chromatography (gradient of 0 to 5% 2 M NH3/MeOH in CH2Cl2) to obtain the title compound as a waxy solid (6.41 g, 57%). ES/MS m/z 291.2 (M+1).

후처리

  1. temperatureHeat
  2. temperatureCool the reaction mixture
  3. extractionextract the mixture with Et2O
  4. washWash the organic layer with H2O
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue

출처 및 근거

ORD 기록
ord-66af781fdcc84ea4a071ab1063a6dc9f
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445493B2

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