p-Toluenesulfonic acid → 5-(5-Chlorobenzoxazol-2-yl)-1-(3,3,3-trifluoropropyl)benzimidazole

HRID 74320

反応式

HRID 74320 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:17][CH2:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[C:14]([CH:16]=3)[NH2:15])=[N:7][C:6]=2[CH:24]=1.[C:25]1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C(OCC)(OCC)OCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]4[N:17]([CH2:18][CH2:19][C:20]([F:21])([F:23])[F:22])[CH:25]=[N:15][C:14]=4[CH:16]=3)=[N:7][C:6]=2[CH:24]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 674982645-Chloro-2-(2-(3,3,3-trifluoropropyl)aminoanilin-5-yl)benzoxazole

生成物 1

HCID 674982605-(5-Chlorobenzoxazol-2-yl)-1-(3,3,3-trifluoropropyl)benzimidazole収率 598%

試薬・触媒・溶媒 1

HCID 31214Ethyl orthoformate溶媒

反応条件

温度
100 °C

実験手順

To a solution of 5-chloro-2-(2-(3,3,3-trifluoropropyl)aminoanilin-5-yl)benzoxazole (see Working Example 138-1) (200 mg, 0.562 mmol) in triethyl orthoformate (5 mL) was added p-toluenesulfonic acid (10 mg), and this was stirred at 100° C. for 4 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with chloroform. The organic layer obtained was dried over anhydrous sodium sulfate, filtered, and concentrated to give crude crystals that were washed with diethyl ether and ethyl acetate to yield the title compound (127 mg, 62% yield) as light yellow crystals.

後処理

  1. extractionthis was extracted with chloroform
  2. customThe organic layer obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude crystals that
  7. washwere washed with diethyl ether and ethyl acetate

出典と根拠

ORDレコード
ord-2833ca671160462685176534e65d63e7
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

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