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

HRID 129188

반응식

HRID 129188 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-897da716db0f433e84a919fc5ef2e197
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466817

연결된 노트

불러오는 중…