Hydrochloric Acid → 2-Chloro-4-methylbenzothiazole

HRID 9566

반응식

HRID 9566 반응식
N(OCCC(C)C)=O.N[C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:13]=2[N:14]=1.[ClH:20]>C(#N)C.[Cu](Cl)Cl>[Cl:20][C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:13]=2[N:14]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 151322-Amino-4-methylbenzothiazole

생성물 1

HCID 20498602-Chloro-4-methylbenzothiazole수율 71%

시약·촉매·용매 2

HCID 24014Cupric Chloride촉매HCID 6342Acetonitrile용매

실험 절차

To a solution containing copper chloride (II) (1.96 g, 14.61 mmol) and tri(ethylene glycol) dimethyl ether (6 mL) in acetonitrile (100 mL) was added isoamyl nitrite (2.14 g, 18.27 mmol), and the reaction mixture was stirred at rt for 30 minutes. To this suspension was added dropwise a solution of 2-amino-4-methylbenzothiazole (2.0 g, 12.18 mmol) in tri(ethylene glycol) dimethyl ether (10 mL). The reaction mixture was stirred at rt for 10 minutes, and then heated at 50° C. for 2.5 h. The reaction mixture was cooled to rt, and then poured cautiously into cold aqueous 6 M HCl (400 mL). The solution was extracted with EtOAc. The organic layer was washed with HCl (1.0 M), water, brine, filtered and concentrated in vacuo. The residue was purified by flash chromatography (Biotage Flash 40M) using 5% ethyl acetate in hexane to afford 2-chloro-4-methyl-1,3-benzothiazole (1.6 g, 71%). 1H NMR (400 MHz, CD2Cl2) δ 2.70 (s, 3H), 7.32 (m, 2H), 7.64 (m, 1H).

후처리

  1. stirringThe reaction mixture was stirred at rt for 10 minutes
  2. temperatureheated at 50° C. for 2.5 h
  3. temperatureThe reaction mixture was cooled to rt
  4. extractionThe solution was extracted with EtOAc
  5. washThe organic layer was washed with HCl (1.0 M), water, brine
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (Biotage Flash 40M)

출처 및 근거

ORD 기록
ord-d8bad3c990f7478fabae4a1573965eda
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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