N,N'-Dimethylethylenediamine → Methyl N-[(Z)-3-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-1-methyl-prop-1-enyl]-N-methyl-carbamate

HRID 918757

反応式

HRID 918757 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[C:16](\I)/[CH3:17])=[N:9]2)=[CH:4][CH:3]=1.[CH3:19][O:20][C:21](=[O:24])[NH:22][CH3:23].P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>C1(C)C=CC=CC=1.[Cu](I)I>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][C:10]([O:13][CH2:14]/[CH:15]=[C:16](\[N:22]([CH3:23])[C:21](=[O:24])[O:20][CH3:19])/[CH3:17])=[N:9]2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 81151Methyl methylcarbamateHCID 896503821-(4-chlorophenyl)-3-[(Z)-3-iodobut-2-enoxy]pyrazole

生成物 1

HCID 89651146Methyl N-[(Z)-3-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-1-methyl-prop-1-enyl]-N-methyl-carbamate

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 1140Toluene溶媒

実験手順

1.50 g (4.00 mmol) 1-(4-chlorophenyl)-3-[(Z)-3-iodobut-2-enoxy]pyrazole, 0.43 g (4.81 mmol) N-methylcarbamic acid methyl ester (9), 76 mg (0.4 mmol) copperiodide, 1.27 g (6.00 mmol) potassium phosphate and 71 mg (0.80 mmol) N,N′-dimethylethylene diamine in 14 ml toluene have been stirred for 1.5 d at 100° C. After removal of the solvents in vacuo the crude product has been purified by chromatography on 50 g silica with MTBE/hexane (1:3). Yield 0.67 g. 1H-NMR (CDCl3): δ=1.90 (s); 3.05 (s); 3.70 (s); 4.68 (m); 5.63 (m); 5.90 (d); 7.35 (m); 7.55 (m); 7.68 (d).

後処理

  1. customAfter removal of the solvents in vacuo the crude product
  2. customhas been purified by chromatography on 50 g silica with MTBE/hexane (1:3)

出典と根拠

ORDレコード
ord-a51a2316363c48bf8c622d7276414bee
出典データセット
uspto-grants-2016_03
特許番号
US09271501B2

関連ノート

読み込み中…