4-Aminobenzonitrile → 4-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]benzonitrile

HRID 128762

反応式

HRID 128762 の反応式
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]1[C:14](=O)[C:15](=[O:20])[C:16]=1[O:17]CC)[CH3:11]>C(O)C>[O:17]=[C:16]1[C:15](=[O:20])[C:14]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[C:13]1[O:12][CH2:10][CH3:11]

参加物

4

反応物 2

HCID 133964-AminobenzonitrileHCID 123228Diethyl squarate

生成物 1

HCID 108240584-[(2-Ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino]benzonitrile

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

4-Aminobenzonitrile (17.58 g, 149 mmol) was added to a solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (25.31 g, 149 mmol) in absolute ethanol (450 mL). The mixture was heated at reflux overnight and the resulting suspension filtered hot to remove a small amount of a dirty yellow solid (discarded). The filtrate was gradually concentrated to afford several crops of 4-(3,4-dioxo-2-ethoxy-cyclobut-1-enylamino)benzonitrile, as a bright yellow solid, which were collected by filtration and combined. Yield: 29.11 g (81%): 1H NMR (DMSO-d6): δ11.07 (s, 1H), 7.81 (d, 2H), 7.56 (d, 2H), 4.79 (q, 2H), 1.46 (t, 3H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationthe resulting suspension filtered hot
  4. customto remove a small amount of a dirty yellow solid (discarded)
  5. concentrationThe filtrate was gradually concentrated

出典と根拠

ORDレコード
ord-6cc25d0e7a23406d92521a7bf8f8a323
出典データセット
uspto-grants-1995_11
特許番号
US05464867

関連ノート

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