Dimethylamine → N,N,3-trimethyl-4-nitrobenzamide

HRID 510475

반응식

HRID 510475 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5](O)=[O:6].C[CH2:15][N:16](C(C)C)[CH:17](C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CNC>CN(C=O)C.O>[CH3:15][N:16]([CH3:17])[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([CH3:1])[CH:3]=1

참가 물질

7

반응물 4

HCID 674DimethylamineHCID 183703-Methyl-4-nitrobenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 786992N,N,3-trimethyl-4-nitrobenzamide수율 73.17%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-methyl-4-nitrobenzoic acid (0.5 g, 2.76 mmol) in DMF (5 mL) was added DIPEA (1.06 g, 8.28 mmol), followed by HATU (1.57 g, 4.14 mmol) and dimethylamine (0.24 g, 5.52 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was then diluted with water and extracted with EtOAc. The organic layer was washed with brine, then concentrated to provide crude material which was further purified by column chromatography (silica:100-200 mesh, MeOH:DCM 8-10%), to afford the title compound (0.42 g, 73.17%). LCMS (ES+) 209 (M+H)+, RT 1.92 minutes (method 3).

후처리

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. concentrationconcentrated
  4. customto provide crude material which
  5. customwas further purified by column chromatography (silica:100-200 mesh, MeOH:DCM 8-10%)

출처 및 근거

ORD 기록
ord-15264fb989334572a52b0318e5672d67
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096614B2

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