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

HRID 450117ノート

反応式

HRID 450117 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f1140ba2357f4cc68ce82a53e0a0b701
出典データセット
uspto-grants-2013_07
特許番号
US08486963B2

反応ノート

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