Hydrochloric Acid → 2-Chloro-6-trifluoromethylbenzothiazole

HRID 9565

反応式

HRID 9565 の反応式
N(OC(C)(C)C)=O.N[C:9]1[S:10][C:11]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.[ClH:22]>C(#N)C.[Cu]>[Cl:22][C:9]1[S:10][C:11]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:12]=2[N:13]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 27359552-Amino-6-(trifluoromethyl)benzothiazole

生成物 1

HCID 114704192-Chloro-6-trifluoromethylbenzothiazole収率 92%

試薬・触媒・溶媒 2

HCID 23978Copper触媒HCID 6342Acetonitrile溶媒2 回

実験手順

In a three-necked flask fitted with a condenser, a suspension of copper II chloride (370 mg, 2.75 mmol) in acetonitrile (5 mL) was treated with tert-butyl nitrite (0.41 mL, 3.44 mmol) and stirred at rt for 10 minutes. A solution of 2-amino-6-trifluoromethylbenzthiazole (500 mg, 2.29 mmol) in acetonitrile (1 mL) was then added dropwise. The mixture was heated at 65° C. for 30 minutes, then cooled and diluted with an excess of 1 N aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate. The organic phase was separated, dried (MgSO4), and concentrated under reduced pressure. An orange semi-solid (501 mg, 92%) was obtained and used without further purification. 1H NMR (300 MHz, CDCl3) δ 8.10–8.05 (m, 2 H), 7.74 (d, 1 H); LC-MS m/z 238.2 (MH+), ret. time 3.76 min TLC Rf=0.50 (9:1 hexanes/ethyl acetate).

後処理

  1. customIn a three-necked flask fitted with a condenser
  2. temperatureThe mixture was heated at 65° C. for 30 minutes
  3. temperaturecooled
  4. extractionThe mixture was extracted with ethyl acetate
  5. customThe organic phase was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c44a57cc9a1c464bb06670086ed74e6d
出典データセット
uspto-grants-2006_08
特許番号
US07091228B2

関連ノート

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