Methylamine → 3-fluoro-N-methyl-5-nitrobenzamide

HRID 522845ノート

反応式

HRID 522845 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5](O)=[O:6].C[CH2:15][N:16](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN>C(Cl)Cl.CCOC(C)=O.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([NH:16][CH3:15])=[O:6]

参加物

8

反応物 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 27590473-Fluoro-5-nitrobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 594427293-fluoro-N-methyl-5-nitrobenzamide収率 90%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a roundbottom flask charged with 3-fluoro-5-nitrobenzoic acid (1.00 g, 5.40 mmol) was added DMF (6.75 mL), followed by Hunig's base (1.13 mL, 6.48 mmol), and HATU (2.157 g, 5.67 mmol). The flask was sealed with a septum and methanamine (2.0 M in THF) (13.5 mL, 27.0 mmol) was added via syringe. The resulting orange reaction mixture was stirred overnight at RT. After 16 h, the reaction mixture was diluted with CH2Cl2 (70 mL) and the resulting mixture was transferred to a separatory funnel and extracted with sat. aq. NaHCO3 (3×30 mL). The organic layer was dried with Na2SO4, filtered and concentrated under reduced pressure. Purification with medium pressure silica gel chromatography using 70:30 Hex:EtOAc as the eluent afforded 3-fluoro-N-methyl-5-nitrobenzamide (961 mg, 4.85 mmol, 90%) as a yellow solid.

後処理

  1. additionwas added via syringe
  2. waitAfter 16 h
  3. customthe resulting mixture was transferred to a separatory funnel
  4. extractionextracted with sat. aq. NaHCO3 (3×30 mL)
  5. dry with materialThe organic layer was dried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification with medium pressure silica gel chromatography

出典と根拠

ORDレコード
ord-dc4c05859e484a4980cbda31e32e6acf
出典データセット
uspto-grants-2016_05
特許番号
US09334269B2

反応ノート

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