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

HRID 2357971

反応式

HRID 2357971 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(C1NC=CN=1)([C:16]1[NH:17][CH:18]=CN=1)=O.CNC>CN(C=O)C>[CH3:16][N:17]([CH3:18])[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

5

反応物 3

HCID 674DimethylamineHCID 183703-Methyl-4-nitrobenzoic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

生成物 1

HCID 786992N,N,3-trimethyl-4-nitrobenzamide収率 75.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Methyl-4-nitrobenzoic acid (3.0 g, 16.56 mmol) in DMF (30 mL) was stirred with carbonyl diimidazole (3.22 g, 1.2 Eq.) for 90 mins. The reaction mixture was cooled in an icebath, and dimethylamine (2 M in THF, 25 mL, 3 Eq.) was added. The mixture was then allowed to warm to room temperature and stirred for 2 hours. The mixture was poured onto ice water (200 ml) and extracted with EtOAc (×6). The combined extracts were washed with brine, dried over MgSO4, filtered and evaporated. Tritration with ether followed by filtration gave N,N,3-trimethyl-4-nitrobenzamide (2.6 g, colourless solid); MS (ES+) 209.

後処理

  1. additionwas added
  2. additionThe mixture was poured onto ice water (200 ml)
  3. extractionextracted with EtOAc (×6)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. filtrationTritration with ether followed by filtration

出典と根拠

ORDレコード
ord-05a17550b5c64f25bc01994f17230e1e
出典データセット
uspto-grants-2010_07
特許番号
US07763629B2

関連ノート

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