4-Nitrophenol → 4-Nitrophenyl 2-nitro-4-(methylsulfonyl)benzoate

HRID 393910ノート

反応式

HRID 393910 の反応式
[N+:1]([C:4]1[CH:12]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[N+:23]([C:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(N(CC)CC)C>CN(C=O)C.ClCCl>[N+:1]([C:4]1[CH:12]=[C:11]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([O:8][C:29]1[CH:30]=[CH:31][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=1)=[O:7])([O-:3])=[O:2]

参加物

7

反応物 4

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 184292Benzoic acid, 4-(methylsulfonyl)-2-nitro-

生成物 1

HCID 226483334-Nitrophenyl 2-nitro-4-(methylsulfonyl)benzoate

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒3 回

実験手順

A 100-mL 2-necked round bottom flask was fitted with thermometer, magnetic stirrer, and reflux condenser with nitrogen bypass. The flask was charged with 1.23 g (5 mmol) of 2-nitro-4-(methylsulfonyl)benzoic acid, 2 drops of DMF, and 20 mL of dichloromethane. Oxalyl chloride (0.70 g, 5.5 mmol) was added dropwise and the mixture was stirred for 1 hr. A solution consisting of 0.70 g (5 mmol) of 4-nitrophenol, 0.55 g (5.5 mmol) of triethylamine and 5 mL of dichloromethane was added and the mixture was stirred for 1 hr. The mixture was diluted with 100 mL of dichloromethane, washed twice with 100 mL portions of aqueous sodium bicarbonate, once with 100 mL of water, dried with magnesium sulfate, filtered, and volatiles removed under reduced pressure to give the title product as 1.56 g of off-white solid, m.p. 171-173° C. 1H NMR (CDCl3): δ 3.19 (s, 3), 7.47 (m, 2), 8.10 (m, 1), 8.38 (m, 3), 8.69 (m, 1).

後処理

  1. customA 100-mL 2-necked round bottom flask was fitted with thermometer, magnetic stirrer
  2. temperaturereflux condenser with nitrogen bypass
  3. additionwas added
  4. stirringthe mixture was stirred for 1 hr
  5. washwashed twice with 100 mL portions of aqueous sodium bicarbonate, once with 100 mL of water
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. customvolatiles removed under reduced pressure

出典と根拠

ORDレコード
ord-e549951fc57b4f08b4567267d290dd2b
出典データセット
uspto-grants-2004_10
特許番号
US06809206B2

反応ノート

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