Diisopropylethylamine → Methyl 3-(N'-hydroxycarbamimidoyl)-4-methylbenzoate

HRID 541184

반응식

HRID 541184 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[NH2:14][OH:15].Cl.C(N(CC)C(C)C)(C)C>O1CCCC1>[OH:15][N:14]=[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:6]([O:8][CH3:9])=[O:7])[NH2:2]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 11819538Methyl 3-cyano-4-methylbenzoate2회

생성물 1

HCID 86672520Methyl 3-(N'-hydroxycarbamimidoyl)-4-methylbenzoate수율 30.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

A mixture of methyl 3-cyano-4-methylbenzoate (compound 1.7, 8 g, 43.38 mmol, 1.00 equiv, 95%), NH2OH.HCl (3.785 g, 54.86 mmol, 1.20 equiv), and N,N-Diisopropylethylamine (DIEA, 17.7 g, 136.95 mmol, 3.00 equiv) in tetrahydrofuran (100 mL) was stirred overnight at 70° C. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was taken up in water and the pH was adjusted to 2-3 with hydrogen chloride (aqueous, 1 M). After washing the mixture with 3×40 mL of ethyl acetate, the pH of the aqueous layer was adjusted to 8-9 with NaOH (aqueous, 2 M) followed by extraction with 3×30 mL of ethyl acetate. The combined organic layers were dried over (Na2SO4) and concentrated under reduced pressure to yield 2.76 g (29%) of the title compound as a white solid.

후처리

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. washAfter washing the mixture with 3×40 mL of ethyl acetate
  4. extractionfollowed by extraction with 3×30 mL of ethyl acetate
  5. dry with materialThe combined organic layers were dried over (Na2SO4)
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4bd0004db68b4c71895dfa665897ebb1
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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