2-Chloroaniline → 3-(2-chloroanilino)-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione

HRID 1743152ノート

反応式

HRID 1743152 の反応式
C(O[C:4]1[C:5](=[O:20])[C:6](=[O:19])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18])C.[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH2:24].C(OC(=O)C)C>CS(C)=O>[Cl:21][C:22]1[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=1[NH:24][C:4]1[C:5](=[O:20])[C:6](=[O:19])[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18]

参加物

5

反応物 3

HCID 72402-ChloroanilineHCID 8857Ethyl AcetateHCID 222385043-ethoxy-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione

生成物 1

HCID 99469493-(2-chloroanilino)-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione収率 41.2%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

A solution of 3-ethoxy-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione (0.38 g, 1.37 mmol) and 2-chloroaniline (0.23 mL, 2.2 mmol) in 2 mL DMSO was heated at 110° C. for overnight. The reaction mixture was cooled to room temperature, and ethylacetate was added, and a precipitate formed. The filtrate was partitioned between ethylacetate and water. The organic layer was dried over sodium sulfate and concentrated. Recrystalized from ethylacetate and hexanes, 203 mg (41%) of 3-(2-chloroanilino)-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione was obtained. LCMS(H+) 360.

後処理

  1. customa precipitate formed
  2. customThe filtrate was partitioned between ethylacetate and water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customRecrystalized from ethylacetate and hexanes

出典と根拠

ORDレコード
ord-1dc49b3fc2ba4802bc8bd61dd3fdc111
出典データセット
uspto-grants-2006_03
特許番号
US07008962B2

反応ノート

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