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

HRID 1743152노트

반응식

HRID 1743152 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1dc49b3fc2ba4802bc8bd61dd3fdc111
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07008962B2

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