Ammonia → 3-(4-Acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dione

HRID 10724

反応式

HRID 10724 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C([O:15][C:16]1[C:17](=O)[C:18](=O)[C:19]=1[O:20]CCCC)CCC.[NH3:27]>C(O)C>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:18]2[C:19](=[O:20])[C:16](=[O:15])[C:17]=2[NH2:27])=[CH:3][CH:4]=1)(=[O:10])[CH3:9]

参加物

5

反応物 3

HCID 222AmmoniaHCID 7468p-AminoacetophenoneHCID 65108Dibutyl squarate

生成物 1

HCID 219810423-(4-Acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dione収率 52.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Ex-102A: To a solution of 2.7 g (20 mmol) of 4′-aminoacetophenone in 90 mL of ethanol, 4.5 g (20 mmol) of 3,4-dibutoxy-3-cyclobutene-1,2-dione (Aldrich) was added. The mixture was then heated to reflux overnight. A light yellow precipitate formed. To the reaction mixture, 20 mL (40 mmol) of ammonia (2.0 M in ethanol) was added, and the resultant mixture was stirred at room temperature for 2 hr. The light yellow solid was filtered and washed with ethanol to give 2.4 g (52%) of 3-(4-acetyl-phenylamino)-4-amino-cyclobut-3-ene-1,2-dione. 1H-NMR (DMSO-d6) δ 9.99 (br, 1H), 7.90 (d, J=8 Hz, 2H), 7.50 (d, J=8 Hz, 2H), 4.31 (br, 2H), 2.48 (s, 3H). HMRS (EI) calcd. for C12H10N2O3: 230.0691; found: 230.0691.

後処理

  1. temperatureThe mixture was then heated
  2. temperatureto reflux overnight
  3. customA light yellow precipitate formed
  4. filtrationThe light yellow solid was filtered
  5. washwashed with ethanol

出典と根拠

ORDレコード
ord-607dcb3ea567495abab93b0af0ab0fe9
出典データセット
uspto-grants-2006_08
特許番号
US07094801B2

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