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Toluene → 7-Bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17305
ノート
印刷プレビュー

反応式

HRID 17305 の反応式
BrC1C(O)=C([C:9]2([C:12](N)=[O:13])[CH2:11][CH2:10]2)C(C#N)=C(C)C=1C1C=CC=CC=1.C1(C(O[C:30]2([NH2:46])[C:35]([C:36]#[N:37])=[C:34]([CH3:38])[C:33]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:32]([Br:45])[CH2:31]2)=O)CC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[Br:45][C:32]1[C:33]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[C:34]([CH3:38])[C:35]([C:36]#[N:37])=[C:30]2[C:31]=1[O:13][C:12]([CH:9]1[CH2:11][CH2:10]1)=[N:46]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86630815(2-Bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide 4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate

生成物 1

HCID 685852697-Bromo-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile収率 85.7%

試薬・触媒・溶媒 1

HCID 8857
Ethyl Acetate
溶媒

実験手順

Next, a mixture of (2-bromo-5-cyano-3-hydroxy-6-methylbiphenyl-4-yl)cyclopropanecarboxamide/4-amino-2-bromo-5-cyano-6-methylbiphenyl-4-yl cyclopropanecarboxylate mixture (160 mg, 0.426 mmol), p-toluenesulfonic acid monohydrate (24 mg, 0.128 mmol) and toluene (13 ml) was heated under reflux for 1.5 hours. After cooling, the reaction liquid was diluted with ethyl acetate, successively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine, dried on anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure to obtain a pale brown residue. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the entitled compound (129 mg) as a colorless solid.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureAfter cooling
  4. customthe reaction liquid
  5. washsuccessively washed with an aqueous saturated sodium hydrogencarbonate solution and saturated brine
  6. dry with materialdried on anhydrous magnesium sulfate
  7. customthe solvent was evaporated away under reduced pressure
  8. customto obtain a pale brown residue
  9. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-0b75770d7e314c74a417b15c56735c91
出典データセット
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07737166B2

反応ノート

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