Chloroacetonitrile → 3-Amino-5-phenylselenophene-2-carbonitrile

HRID 1097220ノート

反応式

HRID 1097220 の反応式
[Se-2:1].[Na+].[Na+].Cl[C:5]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[CH:6][C:7]#[N:8].Cl[CH2:16][C:17]#[N:18].C[O-].[Na+]>CN(C=O)C.CO.O>[NH2:8][C:7]1[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[Se:1][C:16]=1[C:17]#[N:18]

参加物

8

反応物 4

HCID 7856ChloroacetonitrileHCID 73973Sodium selenideHCID 27775113-Chloro-3-phenyl-2-propenenitrileHCID 10942334Sodium Methoxide

生成物 1

HCID 866468883-Amino-5-phenylselenophene-2-carbonitrile収率 53%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
65 °C

実験手順

To a suspension of sodium selenide (4.62 g, 36.7 mmol, prepared from 2.9 g of selenium as described above) in DMF (37 mL) was added a solution of 3-chloro-3-phenylprop-2-enenitrile (6.0 g, 36.7 mmol) in DMF (14 mL) at rt for 5 min and stirred the mixture at 60-70° C. for 2 h. Then chloroacetonitrile (2.32 mL, 36.7 mmol) was added dropwise to the reaction mixture and again stirred at 60-70° C. for 2 h. Then, a solution of sodium methoxide (2.0 g, 36.7 mmol) in dry methanol (23 mL) was added dropwise and stirring was continued for 1 h at the same temperature. The mixture was allowed to room temperature (rt) and poured into cold water and stirred for 15 min. The precipitated solid was filtered and washed with water. The solid was recrystallized from chloroform-hexane to give the product as a brown color solid (4.8 g, 53%), mp 162-164° C. (decomp). 1H NMR (400 MHz, CDCl3): δ 7.46-7.49 (2H, m, Ar—H), 7.37-7.39 (3H, m, Ar—H), 7.01 (1H, s, H-4), 4.55 (2H, br s, —NH2).

後処理

  1. stirringagain stirred at 60-70° C. for 2 h
  2. stirringstirring
  3. waitwas continued for 1 h at the same temperature
  4. customwas allowed to room temperature
  5. custom(rt)
  6. stirringstirred for 15 min
  7. filtrationThe precipitated solid was filtered
  8. washwashed with water
  9. customThe solid was recrystallized from chloroform-hexane

出典と根拠

ORDレコード
ord-abb2273e242c434898075d73e51d5a62
出典データセット
uspto-grants-2012_03
特許番号
US08143237B2

反応ノート

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