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

HRID 968279

반응식

HRID 968279 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 6344Dichloromethane용매

반응 조건

온도
23 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-f7c57f0be0b249669a07bf1fc0fe9b4e
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06958347B2

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