Dimethylformamide → N-(2-Fluoro-4-iodo-phenyl)-malonamic acid ethyl ester

HRID 450113노트

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HRID 450113 반응식
[F:1][C:2]1[CH:8]=[C:7]([I:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N([CH2:15][CH3:16])CC)C.C([CH:19]([C:23](Cl)=[O:24])[C:20](Cl)=[O:21])C.CN(C=[O:30])C>CN(C1C=CN=CC=1)C>[CH2:15]([O:30][C:23](=[O:24])[CH2:19][C:20]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([I:9])=[CH:8][C:2]=1[F:1])=[O:21])[CH3:16]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 1856942-Fluoro-4-iodoanilineHCID 109209242-Ethylpropanedioyl dichloride

생성물 1

HCID 67234460N-(2-Fluoro-4-iodo-phenyl)-malonamic acid ethyl ester수율 87%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

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온도
60 °C

실험 절차

To a solution of 2-fluoro-4-iodoaniline (15.1 g, 63.7 mmol), triethylamine (8.9 mL, 63.7 mmol) and DMAP (100 mg, 0.8 mmol) in DMF (45 mL) was added ethyl malonyl chloride (9.8 mL, 76.4 mmol). The reaction mixture was heated at 60° C. for 2 hours then concentrated in vacuo. The resultant residue was dissolved in ethyl acetate (30 mL), washed with water (20 mL) and the aqueous fraction extracted twice with ethyl acetate (2×10 mL). The combined organic fractions were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 20-30% ethyl acetate in cyclohexane) to yield the title compound as a white solid (19.5 g, 87%). LCMS (Method B): RT=3.43 min, M+H+=352.

후처리

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe resultant residue was dissolved in ethyl acetate (30 mL)
  3. washwashed with water (20 mL)
  4. extractionthe aqueous fraction extracted twice with ethyl acetate (2×10 mL)
  5. washThe combined organic fractions were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-b29dd994dac642ed97e61a6e36b6fd05
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486963B2

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