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

HRID 17305
노트
인쇄 미리보기

반응식

HRID 17305 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8857
Ethyl Acetate
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0b75770d7e314c74a417b15c56735c91
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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