Diethyl squarate → 4-(2-Ethoxy-3,4-dioxo-cyclobut-1-enylamino)-3-ethylbenzonitrile

HRID 1733900

반응식

HRID 1733900 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH2:10][CH3:11].[CH2:12]([O:14][C:15]1[C:16](=O)[C:17](=[O:22])[C:18]=1[O:19]CC)[CH3:13]>C(#N)C.C(OCC)(=O)C>[O:19]=[C:18]1[C:17](=[O:22])[C:16]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=2[CH2:10][CH3:11])=[C:15]1[O:14][CH2:12][CH3:13]

참가 물질

5

반응물 2

HCID 123228Diethyl squarate2회HCID 27353304-Amino-3-ethylbenzonitrile

생성물 1

HCID 199729184-(2-Ethoxy-3,4-dioxo-cyclobut-1-enylamino)-3-ethylbenzonitrile수율 24%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

4-Amino-3-ethylbenzonitrile (2.00 g, 13.7 mmol) was added to a solution of 3,4-diethoxy-3-cyclobutene-1,2-dione (2.30 g, 13.5 mmol) in acetonitrile (5 mL). After refluxing the mixture for 24 h a second portion of 3,4-diethoxy-3-cyclobutene-1,2-dione (1.15 g, 6.76 mmol) was added and heating was continued for an additional 24 h. The reaction mixture was diluted with ethyl acetate (45 mL), stirred vigorously and filtered free of undissolved solid. The filtrate was concentrated and the resulting residue was purified by chromatographed (CH3OH/CH2Cl2) and trituration with ether to afford 0.86 g (24%) of product as a light yellow solid: 1H NMR (DMSO-d6): δ 10.57 (s, 1H), 7.77-7.66 (m, 2H), 7.31 (d, 1H), 4.71 (q, 2H), 2.73 (q, 2H), 1.37 (t, 3H), 1.13 (t, 3H).

후처리

  1. additionwas added
  2. temperatureheating
  3. filtrationfiltered free of undissolved solid
  4. concentrationThe filtrate was concentrated
  5. customthe resulting residue was purified
  6. customby chromatographed (CH3OH/CH2Cl2) and trituration with ether

출처 및 근거

ORD 기록
ord-cc97b40a15064c2d81a778b15be983aa
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05532245

연결된 노트

불러오는 중…