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

HRID 393910노트

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HRID 393910 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 6344Dichloromethane용매3회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e549951fc57b4f08b4567267d290dd2b
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809206B2

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