Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 6-Bromo-7-fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17365노트

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HRID 17365 반응식
[Br:1][C:2]1[C:7]([F:8])=[C:6](O)[C:5]([NH:10][C:11](=[O:17])[C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])=[C:4]([C:18]#[N:19])[C:3]=1[CH3:20].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([F:8])=[C:6]2[O:17][C:11]([C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])=[N:10][C:5]2=[C:4]([C:18]#[N:19])[C:3]=1[CH3:20]

참가 물질

5

반응물 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86630842N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-3-hydroxy-2,2-dimethyl-1-propanamide

생성물 1

HCID 685850036-Bromo-7-fluoro-2-(2-hydroxy-1,1-dimethylethyl)-5-methyl-1,3-benzoxazole-4-carbonitrile수율 54%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

N-(4-Bromo-2-cyano-5-fluoro-6-hydroxy-3-methylphenyl)-3-hydroxy-2,2-dimethyl-1-propanamide (I-107) (1.80 g, 5.21 mmol) was dissolved in toluene (36 ml), pyridinium p-toluenesulfonate (262 mg, 1.04 mmol) was added, followed by heating under reflux for 28 hours. After cooling to room temperature, this was diluted with ethyl acetate, and washed with aqueous sodium hydrogencarbonate solution and saturated brine. The obtained organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure. The resulting residue was recrystallized and purified with n-hexane/ethyl acetate to obtain the entitled compound (912.6 mg, 54%) as a white solid. The filtrate was concentrated under reduced pressure to obtain a crude form (514.3 mg, 30%) as a pale yellow oily substance.

후처리

  1. temperatureby heating
  2. temperatureunder reflux for 28 hours
  3. washwashed with aqueous sodium hydrogencarbonate solution and saturated brine
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. customThe resulting residue was recrystallized
  7. custompurified with n-hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-42157eb6382648df99d975387e42a2c2
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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