1,2-Ethanediamine, N1-phenyl- → N-(6-Cyano-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-N'-phenylethylenediamine

HRID 129188

反応式

HRID 129188 の反応式
Br[CH:2]1[C:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]=2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3]1.[C:16]1([NH:22][CH2:23][CH2:24][NH2:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>CN(C)C=O>[C:12]([C:9]1[CH:10]=[CH:11][C:6]2[O:5][C:4]([CH3:15])([CH3:14])[CH2:3][CH:2]([NH:25][CH2:24][CH2:23][NH:22][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[CH:8]=1)#[N:13]

参加物

5

反応物 3

HCID 742701,2-Ethanediamine, N1-phenyl-HCID 516892Sodium BicarbonateHCID 102446284-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

生成物 1

HCID 19373592N-(6-Cyano-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-yl)-N'-phenylethylenediamine収率 409.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (0.75 g, 2.82 mmole, from Example 8,part B) and N-phenylethylenediamine (8.84 g, 10 eq.) containing NaHCO3 (2.40 g, 5 eq.) in N,N-dimethylformamide (15 ml) was stirred for 48 hours at room temperature. The reaction mixture was partitioned between ethyl acetate and distilled H2O. The organic phase was washed with distilled H2O, saturated NaCl solution, dried over Na2SO4 and evaporated in vacuo to obtain 3.71 g of an orange gum. The crude product was chromatographed on silica eluting with 3:2 hexane/ethyl acetate to obtain 0.36 g (40%) of the title compound as a colorless gum which solidified upon standing. 1H NMR (CDCl3) δ7.91 (s, 1H), 7.38 (dd, J=2.34 and 8.79 Hz, 1H), 7.19 (m, 2H), 6.79 (d, J=8.21 Hz, 1H), 6.70 (m, 3H), 3.87 (dd, J=5.86 and 11.14 Hz, 1H), 3.26 (m, 2H), 3.10 (m, 1H), 2.86 (m, 1H), 2.20 (dd, J=5.87 and 12.90 Hz, 1H), 1.58 (d, J=12.30 Hz, 1H), 1.45 (s, 3H), 1.27 (s, 3H); 13C NMR (CDCl3) δ157.63, 148.16, 132.40, 132.09, 129.21, 125.32, 119.56, 118.09, 117.52, 112.97, 102.89, 76.83, 49.24, 44.89, 44.00, 39.25, 29.69, 24.96; MS: (M+H)+ @322.

後処理

  1. customThe reaction mixture was partitioned between ethyl acetate
  2. distillationdistilled H2O
  3. washThe organic phase was washed with distilled H2O, saturated NaCl solution
  4. dry with materialdried over Na2SO4
  5. customevaporated in vacuo

出典と根拠

ORDレコード
ord-897da716db0f433e84a919fc5ef2e197
出典データセット
uspto-grants-1995_11
特許番号
US05466817

関連ノート

読み込み中…