Methanol → (E)-ethyl 3-(4-acetamido-3-(2-methoxyethoxy)phenylamino)-2-cyanoacrylate

HRID 403652노트

반응식

HRID 403652 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[NH:15][C:16](=[O:18])[CH3:17].CO.[H][H].[C:23](/[C:25](=[CH:31]\OCC)/[C:26]([O:28][CH2:29][CH3:30])=[O:27])#[N:24]>[Pd].C1COCC1.C1(C)C=CC=CC=1.C(O)(=O)C>[C:16]([NH:15][C:7]1[CH:8]=[CH:9][C:10]([NH:12]/[CH:31]=[C:25](\[C:23]#[N:24])/[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:11][C:6]=1[O:5][CH2:4][CH2:3][O:2][CH3:1])(=[O:18])[CH3:17]

참가 물질

9

반응물 4

HCID 887MethanolHCID 1715183Ethyl 2-cyano-3-ethoxyacrylateHCID 67287383N-(2-(2-methoxyethoxy)-4-nitrophenyl)acetamideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 67474100(E)-ethyl 3-(4-acetamido-3-(2-methoxyethoxy)phenylamino)-2-cyanoacrylate수율 75.1%

시약·촉매·용매 4

HCID 23938Palladium촉매HCID 176Acetic Acid용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

To N-(2-(2-methoxyethoxy)-4-nitrophenyl)acetamide (75 g, 0.295 mol, 1.00 equiv) was added methanol (600 ml), 10% Pd/C (6 g), and glacial acetic acid (60 ml) in a vessel which subject to a closed pressure vessel. Replacement of Kettle access from air to 5 atm hydrogen at room temperature was deployed and reacted for 5 hours. The reaction mixture was filtered, and concentrated. Toluene (440 ml), THF (220 ml), and (E)-ethyl 2-cyano-3-ethoxyacrylate (76 g, 0.497 mol, 1.68 equiv) were added and then refluxed for 16 h. The reaction mixture was cooled to room temperature, filtered, washed and dried with tetrahydrofuran to give 77 g product as off-white solid. MS (ESI) m/z: 347 (M+1).

후처리

  1. customsubject to a closed pressure vessel
  2. customat room temperature
  3. customreacted for 5 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated
  6. temperaturerefluxed for 16 h
  7. filtrationfiltered
  8. washwashed
  9. dry with materialdried with tetrahydrofuran

출처 및 근거

ORD 기록
ord-c3276314a347489790600ba719f9412d
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748453B2

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