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

HRID 39337

反応式

HRID 39337 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-d3b48ac36ef04da0a64fbe747cc56d37
出典データセット
uspto-grants-2013_09
特許番号
US08524902B2

関連ノート

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