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

HRID 260799

반응식

HRID 260799 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 34%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
150 °C

실험 절차

4-Amino-3-ethylbenzonitrile (0.86 g, 5.88 mmol) and 3,4-diethoxy-3-cyclobutene-1,2-dione (1.0 g, 5.88 mmol) in acetonitrile (2 mL) was heated in an oil bath at 110° C. for 21 hours. 3,4-Diethoxy-3-cyclobutene-1,2-dione (0.5 g, 2.9 mmol) was added to the reaction mixture and the temperature of the oil bath increased to 150° C. After 48 hours the reaction mixture was cooled to room temperature, then diluted with ethyl acetate and filtered. The filtrate was concentrated and the resulting solid was taken up in ethyl acetate (5 mL) and sonicated. Filtration gave 0.54 g (34%) of 4-(3,4-dioxo-2-ethoxy-cyclobut-1-enylamino)-3-ethylbenzonitrile as a light brown solid: 1H NMR (DMSO-d6): δ 10.56 (br s, 1H), 7.70 (br s overlapping a doublet at δ 7.69, 2H), 7.30 (d, 1H), 4.71 (q, 2H), 2.74 (q, 2H), 1.37 (t, 3H), 1.15 (t, 3H).

후처리

  1. temperatureAfter 48 hours the reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customsonicated
  5. filtrationFiltration

출처 및 근거

ORD 기록
ord-72ab03e7554b4b568883a777a1c795e1
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05530025

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