4-Methoxy-3-nitrobenzaldehyde → Ethanol, reaction products with ammonia, distn. residues

HRID 1633718

反応式

HRID 1633718 の反応式
I[C:2]1[N:3]=[CH:4][N:5](S(N(C)C)(=O)=O)[CH:6]=1.C([Mg]Br)C.[CH3:17][O:18][C:19]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1>ClCCl>[CH2:19]([OH:18])[CH3:20].[NH3:3].[NH:5]1[CH:6]=[C:2]([CH:23]([C:22]2[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[C:26]([N+:27]([O-:29])=[O:28])[CH:25]=2)[OH:24])[N:3]=[CH:4]1

参加物

6

反応物 3

HCID 7006084-Methoxy-3-nitrobenzaldehydeHCID 2773390N,N-Dimethyl 4-iodo-1H-imidazole-1-sulfonamideHCID 178418443HCID 178418443、化合物

生成物 2

HCID 22020343Ethanol, reaction products with ammonia, distn. residues収率 20%HCID 178491310HCID 178491310、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A solution of 4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide (3.0 g, 10 mmol) in dichloromethane (40 mL) under nitrogen was treated with ethylmagnesium bromide (3.0 M in diethyl ether, 3.3 mL) over 2 minutes, stirred for 30 minutes, treated with 4-methoxy-5-nitrobenzaldehyde (2.0 g, 11 mmol), stirred for 1 hour, stored at 0° C. for 16 hours, concentrated to dryness, treated with 1M HCl(100 mL), heated to 100° C. for 16 hours, cooled to ambient temperature, neutralized with NaHCO3 and extracted with 3:1 dichloromethane:ethanol (5×). The combined extractions were dried (MgSO4), filtered and concentrated. Purification on silica gel with 10% and then 20% ethanol/ammonia-saturated dichloromethane provided the desired compound.

後処理

  1. stirringstirred for 1 hour
  2. waitstored at 0° C. for 16 hours
  3. concentrationconcentrated to dryness
  4. additiontreated with 1M HCl(100 mL)
  5. temperaturecooled to ambient temperature
  6. extractionextracted with 3:1 dichloromethane
  7. extractionThe combined extractions
  8. dry with materialwere dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customPurification on silica gel with 10%

出典と根拠

ORDレコード
ord-cc3d2391fc2842d9833404e6d64bd57c
出典データセット
uspto-grants-2003_01
特許番号
US06503935B1

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