N-Benzylethylenediamine → HCID 19373577、化合物

HRID 129190

反応式

HRID 129190 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.[CH2:16]([NH:23][CH2:24][CH2:25][NH2:26])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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:26][CH2:25][CH2:24][NH:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:7]=2[CH:8]=1)#[N:13]

参加物

5

反応物 3

HCID 77801N-BenzylethylenediamineHCID 516892Sodium BicarbonateHCID 102446284-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran

生成物 1

HCID 19373577HCID 19373577、化合物収率 216.7%

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 (1.50 g, 5.64 mmole, from Example 8,part B) and N-benzylethylenediamine (8.48 g, 10 eq.) containing NaHCO3 (4.80 g, 5 eq.) in N,N-dimethylformamide (30 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 4.10 g of an orange oil. The crude product was chromatographed on silica eluting with 9:1 methylene chloride/methanol (trace of NH4OH) to obtain 0.91 g (48%) of the title compound as a colorless gum. 1H NMR (CDCl3) δ8.00 (s, 1H), 7.49-7.34 (m, 6H), 6.88 (d, J=8.80 Hz, 1H), 3.93-3.82 (m, 3H), 3.03-2.80 (m, 5H), 2.25 (dd, J= 5.57 and 13.20 Hz, 1H), 1.67 (m, 1H), 1.53 (s, 3H), 1.35 (s, 3H); 13C NMR (CDCl3) δ157.66, 139.89, 132.52, 132.03,128.43, 128.14, 127.05, 125.55, 119.65, 118.06, 102.89, 76.86, 53.73, 49.38, 49.01, 45.32, 39.25, 36.40, 29.72, 25.02; MS: (M+H)+ @334.

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-c32d432b872c430a84fda0ddcc852de9
出典データセット
uspto-grants-1995_11
特許番号
US05466817

関連ノート

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