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

HRID 522845노트

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HRID 522845 반응식
[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]

참가 물질

8

반응물 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)

생성물 1

HCID 594427293-fluoro-N-methyl-5-nitrobenzamide수율 90%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dc4c05859e484a4980cbda31e32e6acf
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334269B2

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