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

HRID 14486

反応式

HRID 14486 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-24bdd29273584eb289dff4c68aa8064e
出典データセット
uspto-grants-2010_06
特許番号
US07732435B2

関連ノート

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