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

HRID 510475

反応式

HRID 510475 の反応式
[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

参加物

7

反応物 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)

生成物 1

HCID 786992N,N,3-trimethyl-4-nitrobenzamide収率 73.17%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-15264fb989334572a52b0318e5672d67
出典データセット
uspto-grants-2015_08
特許番号
US09096614B2

関連ノート

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