1,1'-Carbonyldiimidazole → 2-amino-N,6-dimethoxybenzamide

HRID 1045972

반응식

HRID 1045972 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([OH:6])=O.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1.C([N:28](C(C)C)CC)(C)C>C1COCC1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH:28][O:19][CH3:18])=[O:6]

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 27353572-Amino-6-methoxybenzoic Acid

생성물 1

HCID 569516592-amino-N,6-dimethoxybenzamide수율 33.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
21 °C

실험 절차

A mixture of 2-amino-6-methoxybenzoic acid (4.6 g, 27.52 mmol) and carbonyl-1,1′-dimidazole (5.35 g, 33.02 mmol) in THF (70 ml) was stirred at 21° C. under nitrogen for 3 days. N,N-diisopropyl-N-ethyl-amine (1.667 ml, 9.57 mmol) and O-methylhydroxylaminehydrochloride (0.545 ml, 7.18 mmol) were added. The solution was heated to 50° C. for 3 hours. After cooling and concentration under vacuum, the reaction mixture was diluted with EtOAc, washed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine, dried over magnesium sulfate, concentrated under vacuum. The residue was purified by flash chromatography on silica gel eluting with 10 to 20% EtOAc in DCM to afford 2-amino-N,6-dimethoxybenzamide (318 mg, 33.9%) as a white solid. Mass spectrum: MH+ 197; NMR Spectrum: (DMSOd6) 3.67 (s, 3H), 3.71 (s, 3H), 5.57 (bs, 2H), 6.19 (d, 1H), 6.31 (d, 1H), 7.02 (dd, 1H)

후처리

  1. temperatureThe solution was heated to 50° C. for 3 hours
  2. temperatureAfter cooling
  3. concentrationconcentration under vacuum
  4. additionthe reaction mixture was diluted with EtOAc
  5. washwashed with a saturated aqueous solution of sodium hydrogencarbonate, water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by flash chromatography on silica gel eluting with 10 to 20% EtOAc in DCM

출처 및 근거

ORD 기록
ord-4eeda08fd5ba448a9af5234e19039102
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569298B2

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