N-Ethylaniline → N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide

HRID 968279ノート

反応式

HRID 968279 の反応式
C(Cl)(=O)C(Cl)=O.[I:7][C:8]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=O.C(N(CC)CC)C.[CH2:27]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH3:28]>ClCCl.CN(C1C=CN=CC=1)C.O.CN(C)C=O>[CH2:27]([N:29]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:10](=[O:12])[C:9]1[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:8]=1[I:7])[CH3:28]

参加物

9

反応物 4

HCID 7670N-EthylanilineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 4589642-Iodo-4-nitrobenzoic acid

生成物 1

HCID 22288547N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide収率 93%

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

Oxalyl chloride (12 ml, 17.3 g, 0.14 mol) was added dropwise to a solution of 2-iodo-4-nitrobenzoic acid I-1 b (20 g, 68.3 mmol) in dichloromethane (137 ml). N,N-Dimethylformamide (0.1 ml) was added to the reaction mixture via syringe, the reaction mixture was stirred at 23° C. for 1 hour, and another portion of N,N-dimethylformamide (0.1 ml) was added. After stirring the reaction mixture another 2 hours, the reaction mixture was concentrated in vacuo. The residue was taken up in dichloromethane (137 ml), and DMAP (50 mg) and triethylamine (14.3 ml, 10.3 g, 0.102 mol) were added. The mixture was cooled to 0° C. and N-ethylaniline (10.1 ml, 9.9 g, 82 mmol) was added over a 10 min period. The reaction mixture was warmed to 23° C. After 16 hours at this temperature, water (150 ml) was added, and the layers were separated. The organics were washed with 1 N HCl (2 100-ml portions), dried over anhydrous sodium sulfate, and were concentrated. Purification of the residue by flash column chromatography (dichloromethane) afforded N-ethyl-2-iodo-4-nitro-N-phenyl-benzamide I-1c (24.3 g, 93%).

後処理

  1. stirringAfter stirring the reaction mixture another 2 hours
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. temperatureThe mixture was cooled to 0° C.
  4. temperatureThe reaction mixture was warmed to 23° C
  5. customthe layers were separated
  6. washThe organics were washed with 1 N HCl (2 100-ml portions)
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationwere concentrated
  9. customPurification of the residue by flash column chromatography (dichloromethane)

出典と根拠

ORDレコード
ord-f7c57f0be0b249669a07bf1fc0fe9b4e
出典データセット
uspto-grants-2005_10
特許番号
US06958347B2

反応ノート

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