Hydrochloric Acid → 2-Chloro-6-methylbenzothiazole

HRID 70143

反応式

HRID 70143 の反応式
N(OC(C)(C)C)=O.[CH3:8][C:9]1[CH:18]=[CH:17][C:12]2[N:13]=[C:14](N)[S:15][C:11]=2[CH:10]=1.[ClH:19]>CC#N.[Cu](Cl)Cl>[Cl:19][C:14]1[S:15][C:11]2[CH:10]=[C:9]([CH3:8])[CH:18]=[CH:17][C:12]=2[N:13]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 173352-Amino-6-methylbenzothiazole

生成物 1

HCID 20498662-Chloro-6-methylbenzothiazole収率 74%

試薬・触媒・溶媒 2

HCID 24014Cupric Chloride触媒HCID 6342Acetonitrile溶媒

実験手順

t-Butyl nitrite (3.25 mL, 27.4 mmol) was added to a suspension of copper (II) chloride (2.95 g, 22.0 mmol) in CH3CN (31 mL). 6-Methyl-2-aminobenzothiazole (3.0 g, 18 mmol) was added portionwise over ˜30 min., and the reaction mixture was stirred at rt overnight. The reaction mixture was poured into 20% aqueous HCl (100 mL) and was extracted with EtOAc (3×). The combined extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure. The material was purified by column chromatography (0 to 10% EtOAc in Hexanes gradient), yielding 2.50 g (74%) of the title compound as a yellowish oil that solidified on standing. LC-MS: RT=9.71 min., [M+H]+=184.0.

後処理

  1. extractionwas extracted with EtOAc (3×)
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe material was purified by column chromatography (0 to 10% EtOAc in Hexanes gradient)

出典と根拠

ORDレコード
ord-d1962261cd4641f89dd914fb97c5e2ef
出典データセット
uspto-grants-2014_09
特許番号
US08822472B2

関連ノート

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