Diethyl squarate → 3-Ethoxy-4-[(2-hydroxy-6-methylphenyl)amino]-3-cyclobutene-1,2-dione

HRID 357296

反応式

HRID 357296 の反応式
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][CH2:11][O:12][C:13]1[C:17](=O)[C:15](=[O:16])[C:14]=1[O:19]CC>C(O)C>[CH2:11]([O:12][C:13]1[C:14](=[O:19])[C:15](=[O:16])[C:17]=1[NH:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9])[CH3:10]

参加物

4

反応物 2

HCID 123228Diethyl squarateHCID 30141382-Amino-m-cresol

生成物 1

HCID 189374263-Ethoxy-4-[(2-hydroxy-6-methylphenyl)amino]-3-cyclobutene-1,2-dione

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of 2-amino-3-methylphenol (3.6 g, 29.2 mmol) and diethyl squarate (5 g, 29.4 mmol) in dry ethanol (80 mL) was heated to reflux for two days, then allowed to stand at room temperature for 48 hours. The reaction mixture was concentrated under reduced pressure and the resulting residue was suspended in ethyl acetate (50 mL). Hexane (50 mL) was added to produce a slurry, which was filtered, and rinsed with three portions of hexane:ethyl acetate (1:1). The resulting solid was suspended in dichloromethane (200 mL) and methanol (20 mL), stirred at room temperature for 30 minutes, and filtered. The precipitate was suspended in hot dichloromethane, filtered hot, and dried to give 3-ethoxy-4-(2-hydroxy-6-methylphenylamino)-cyclobut-3-ene-1,2-dione, 1.56 g (6.3 mmol, 22%).

後処理

  1. temperatureto reflux for two days
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionHexane (50 mL) was added
  4. customto produce a slurry, which
  5. filtrationwas filtered
  6. washrinsed with three portions of hexane:ethyl acetate (1:1)
  7. filtrationfiltered
  8. filtrationfiltered hot
  9. customdried

出典と根拠

ORDレコード
ord-ca6c9425068e44fb973eae46052db046
出典データセット
uspto-grants-1998_11
特許番号
US05840764

関連ノート

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