Water → 3-Bromo-2-isopropyl-7-(4-methoxybenzylamino)-8-nitro-chromen-4-one

HRID 14486

반응식

HRID 14486 반응식
[Br:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([N+:26]([O-:28])=[O:27])[C:7](OS(C3C(C)=CC(C)=CC=3C)(=O)=O)=[CH:8][CH:9]=2)[O:4][C:3]=1[CH:29]([CH3:31])[CH3:30].[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1.O>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([N+:26]([O-:28])=[O:27])[C:7]([NH:39][CH2:38][C:37]3[CH:40]=[CH:41][C:34]([O:33][CH3:32])=[CH:35][CH:36]=3)=[CH:8][CH:9]=2)[O:4][C:3]=1[CH:29]([CH3:30])[CH3:31]

참가 물질

5

반응물 3

HCID 962WaterHCID 754524-MethoxybenzylamineHCID 866256152,4,6-trimethyl-benzenesulfonic acid 3-bromo-2-isopropyl-8-nitro-4-oxo-4H-chromen-7-yl ester

생성물 1

HCID 687031553-Bromo-2-isopropyl-7-(4-methoxybenzylamino)-8-nitro-chromen-4-one

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
130 °C

실험 절차

To a solution of 2,4,6-trimethyl-benzenesulfonic acid 3-bromo-2-isopropyl-8-nitro-4-oxo-4H-chromen-7-yl ester (1.906 g, 3.5 mmol) in dry toluene (18 ml) in a 20 ml capacity microwave tube is added p-methoxybenzylamine (0.69 ml, 5.26 mmol). The mixture is heated at 130° C. under microwave irradiation for 90 minutes and then at 140° C. under microwave irradiation for a further 30 minutes. Water (40 ml) is added, and the mixture is extracted with ethyl acetate (3×100 ml). The ethyl acetate extracts are combined, washed with saturated brine (50 ml), dried (MgSO4), filtered and evaporated. The crude product is purified by chromatography on silica gel using cyclohexane-ethyl acetate (8:1) as eluant. The product-containing fractions are evaporated under reduced pressure, and the residue is triturated with diethyl ether to give a pale yellow solid.

후처리

  1. customat 140° C. under microwave irradiation for a further 30 minutes
  2. extractionthe mixture is extracted with ethyl acetate (3×100 ml)
  3. washwashed with saturated brine (50 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified by chromatography on silica gel
  8. customThe product-containing fractions are evaporated under reduced pressure
  9. customthe residue is triturated with diethyl ether
  10. customto give a pale yellow solid

출처 및 근거

ORD 기록
ord-24bdd29273584eb289dff4c68aa8064e
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732435B2

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