Imidazole → 4-bromo-2-methoxy-5-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenol

HRID 41943ノート

反応式

HRID 41943 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([OH:10])=[CH:4][C:3]=1[C:11](=O)[CH3:12].Cl.[N+:15]([C:18]1[CH:26]=[CH:25][C:21]([CH2:22][O:23][NH2:24])=[CH:20][CH:19]=1)([O-:17])=[O:16].N1C=CN=C1.C(OCC)(=O)C.CCCCCC>CCO>[N+:15]([C:18]1[CH:19]=[CH:20][C:21]([CH2:22][O:23]/[N:24]=[C:11](/[C:3]2[CH:4]=[C:5]([OH:10])[C:6]([O:8][CH3:9])=[CH:7][C:2]=2[Br:1])\[CH3:12])=[CH:25][CH:26]=1)([O-:17])=[O:16]

参加物

6

反応物 4

HCID 795ImidazoleHCID 74967Hydroxylamine, O-((4-nitrophenyl)methyl)-, hydrochloride (1:1)HCID 21226206Ethyl acetate hexaneHCID 349091311-(2-Bromo-5-hydroxy-4-methoxyphenyl)ethan-1-one

生成物 1

HCID 251004124-bromo-2-methoxy-5-[(E)-C-methyl-N-[(4-nitrophenyl)methoxy]carbonimidoyl]phenol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A magnetically stirred solution of ketone 39 (162 mg, 0.661 mmol) in EtOH (2.0 mL) was treated with compound 19 (271 mg, 1.32 mmol) and imidazole (68 mg, 0.999 mmol) then the resulting mixture stirred at reflux for 2 h before being cooled and concentrated under reduced pressure. The ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL) and the separated aqueous fraction extracted with CH2Cl2 (1×10 ml). The combined organic fractions were then dried (MgSO4), filtered and concentrated under reduced pressure. The resulting mixture was subjected to flash chromatography (15:85 v/v ethyl acetate/hexane) to afford a ca. 3:1 mixture of the E- and Z-isomeric foams of the title compound CP302108 (229 mg, 88%) as a pale-yellow solid, Rf 0.5 in 1:1 v/v ethyl acetate/hexane. Recrystallisation of this material (twice from isopropanol) afforded the major isomer, CP302108-major, as a pale-yellow solid, m.p. 136.8-138.4° C.

後処理

  1. temperatureat reflux for 2 h
  2. temperaturebefore being cooled
  3. concentrationconcentrated under reduced pressure
  4. customThe ensuing residue was partitioned between CH2Cl2 (10 mL) and H2O (10 mL)
  5. extractionthe separated aqueous fraction extracted with CH2Cl2 (1×10 ml)
  6. dry with materialThe combined organic fractions were then dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford

出典と根拠

ORDレコード
ord-999dc851f1014564b47261f21296e38b
出典データセット
uspto-grants-2013_09
特許番号
US08536157B2

反応ノート

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