Morpholine → Morpholino(3-nitrophenyl)methanone

HRID 1487144

反応式

HRID 1487144 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=O)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C(Cl)Cl.CN(C=O)C>[O:29]1[CH2:30][CH2:31][N:26]([C:7]([C:6]2[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[O:9])[CH2:27][CH2:28]1

参加物

7

反応物 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 84973-Nitrobenzoic acidHCID 65578Oxalyl chloride

生成物 1

HCID 225453Morpholino(3-nitrophenyl)methanone収率 69.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To stirred solution of 3-nitrobenzoic acid (5 g, 29.9 mmol) in DCM: DMF (30 ml, 29:1) was added oxalyl chloride (3.14 ml, 35.9 mmol) dropwise at RT. Resulting reaction mixture was stirred for 1 h. The mixture was concentrated and the residue was dissolved in DCM (25 ml), the reaction mixture was cooled to 0° C. and triethylamine (6.26 ml, 44.9 mmol) and morpholine (3.13 ml, 35.9 mmol) were added and the reaction mixture was stirred for 1 h. The reaction mixture was concentrated under vacuum and the residue was diluted with cold water, the solid separated out was filtered and washed with n-hexanes and dried under vacuum to give the product (4.9 g).

後処理

  1. customResulting
  2. customreaction mixture
  3. concentrationThe mixture was concentrated
  4. dissolutionthe residue was dissolved in DCM (25 ml)
  5. stirringthe reaction mixture was stirred for 1 h
  6. concentrationThe reaction mixture was concentrated under vacuum
  7. additionthe residue was diluted with cold water
  8. customthe solid separated out
  9. filtrationwas filtered
  10. washwashed with n-hexanes
  11. customdried under vacuum

出典と根拠

ORDレコード
ord-2ceddaf9a6db4f9eb02bae758ec6561c
出典データセット
uspto-grants-2016_08
特許番号
US09428499B2

関連ノート

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