1,1-Dimethylhydrazine → N-[(E)-[(E)-3-(4-bromo-2-prop-2-ynoxyphenyl)prop-2-enylidene]amino]-N-methylmethanamine

HRID 870891ノート

反応式

HRID 870891 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH:10]=O)=[C:4]([O:12][CH2:13][C:14]#[CH:15])[CH:3]=1.[O-]S([O-])(=O)=O.[Mg+2].[CH3:22][N:23]([CH3:25])[NH2:24]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH:10]=[N:24]/[N:23]([CH3:25])[CH3:22])=[C:4]([O:12][CH2:13][C:14]#[CH:15])[CH:3]=1

参加物

5

反応物 3

HCID 59761,1-DimethylhydrazineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 866958863-(4-Bromo-2-prop-2-ynyloxy-phenyl)-propenal

生成物 1

HCID 89791447N-[(E)-[(E)-3-(4-bromo-2-prop-2-ynoxyphenyl)prop-2-enylidene]amino]-N-methylmethanamine収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (E)-3-(4-bromo-2-(prop-2-ynyloxy)phenyl)acrylaldehyde (2.85 g, 10.8 mmol) in dichloromethane (200 mL) containing anhydrous MgSO4 (16 g) was cooled in an ice bath with stirring. To the ice-cold solution was added 1,1-dimethylhydrazine (2.45 mL, 32.4 mmol) dropwise and the reaction mixture was allowed to warm up to ambient temperature and was stirred for 18 h. The volatiles were concentrated under reduced pressure and the residue was coevaporated sequentially with dichloromethane (50 mL), dichloroethane (50 mL) and heptane (50 mL). (E)-2-((E)-3-(4-bromo-2-(prop-2-ynyloxy)phenyl)allylidene)-1,1-dimethylhydrazine (2.7 g, 8.79 mmol, 90% yield, 90% purity) was obtained as a yellow powder. 1H NMR (500 MHz, CDCl3) δ 7.39 (d, J=7.9 Hz, 1H), 7.20-7.10 (m, 3H), 7.00-6.86 (m, 2H), 4.75 (d, J=2.3 Hz, 2H), 2.95 (s, 6H), 2.58 (t, J=2.3 Hz, 1H); LCMS (Method B) (ESI) m/e 307.0, 309.0 Br pattern [(M+H)+, calcd for C14H15BrN2O 307.0].

後処理

  1. temperaturewas cooled in an ice bath
  2. stirringwas stirred for 18 h
  3. concentrationThe volatiles were concentrated under reduced pressure

出典と根拠

ORDレコード
ord-cdece5ef261742c8a83a69157c1eea64
出典データセット
uspto-grants-2015_03
特許番号
US08969564B2

反応ノート

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