Ethyl Acetate → 3-(2-Bromoanilino)-4-(2-hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione

HRID 1743151

反応式

HRID 1743151 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.[Br: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>[Br: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 8857Ethyl AcetateHCID 119922-BromoanilineHCID 222385043-ethoxy-4-(2-Hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione

生成物 1

HCID 101793433-(2-Bromoanilino)-4-(2-hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione収率 19%

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 (0.39 g, 1.4 mmol) and 2-bromoaniline (0.36 g, 2.09 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. Titration from acetone and hexanes gave 106 mg (19%) of 3-(2-bromoanilino)-4-(2-hydroxy-4-nitroanilino)-3-cyclobutene-1,2-dione. LCMS(H+) 404

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

出典と根拠

ORDレコード
ord-d51b72e7d92f42fca638e17382a962f7
出典データセット
uspto-grants-2006_03
特許番号
US07008962B2

関連ノート

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