Dimethylformamide → N-(2-Fluoro-4-methylsulfanyl-phenyl)-malonamic acid methyl ester

HRID 450117노트

반응식

HRID 450117 반응식
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10].C(N(CC)CC)C.C[CH:19]([C:23](Cl)=[O:24])[C:20](Cl)=[O:21].CN([CH:29]=[O:30])C>CN(C1C=CN=CC=1)C>[CH3:29][O:30][C:23](=[O:24])[CH2:19][C:20]([NH:10][C:3]1[CH:4]=[CH:5][C:6]([S:8][CH3:9])=[CH:7][C:2]=1[F:1])=[O:21]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10931669MethylmalonylchlorideHCID 220256172-Fluoro-4-(methylsulfanyl)aniline

생성물 1

HCID 67234589N-(2-Fluoro-4-methylsulfanyl-phenyl)-malonamic acid methyl ester수율 72%

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

반응 조건

온도
60 °C

실험 절차

To a solution of 2-fluoro-4-methylsulfanylphenylamine (13 g, 82.7 mmol), triethylamine (9.3 mL, 86.8 mmol) and DMAP (100 mg, 0.8 mmol) in DMF (50 mL) was added methyl malonyl chloride (11.5 mL, 82.7 mmol). The reaction 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 10-30% ethylacetate in cyclohexane) to yield the title compound as a white solid (15.4 g, 72%). LCMS (Method B): RT=2.94 min, M+H+=258.

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-f1140ba2357f4cc68ce82a53e0a0b701
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486963B2

반응 노트

불러오는 중…