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 17365ノート

反応式

HRID 17365 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-42157eb6382648df99d975387e42a2c2
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

反応ノート

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