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Sodium Chloride → 4-Methyl-2-(pyridin-3-yl)-1,3-thiazole-5-amine

HRID 523451
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HRID 523451 반응식
[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[S:5][C:6]=1[N+:7]([O-])=O.[Sn](Cl)Cl.C(OC)(C)(C)C.[Cl-].[Na+]>Cl.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]=[C:4]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[S:5][C:6]=1[NH2:7]
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참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 15413tert-Butyl methyl etherHCID 24479Stannous ChlorideHCID 2176783-(4-Methyl-5-nitro-1,3-thiazol-2-yl)pyridine

생성물 1

HCID 666453454-Methyl-2-(pyridin-3-yl)-1,3-thiazole-5-amine

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매3회
HCID 8857Ethyl Acetate용매

실험 절차

10.1 g (45.6 mmol) of 3-(4-methyl-5-nitro-1,3-thiazol-2-yl)pyridine (for preparation see DE 2221647) were dissolved in 100 ml of 10% hydrochloric acid together with 10 ml of conc. hydrochloric acid, and 25 g of tin(II) chloride dissolved in 10% hydrochloric acid were added in portions, and the mixture was stirred for 1 h (hour), in the course of which heating occurred. The mixture was poured into ice/sodium hydroxide solution, methyl t-butyl ether, ethyl acetate and saturated sodium chloride solution were added, the mixture was extracted 4 times at pH=10 with ethyl acetate, the combined organic phases were dried with MgSO4 and the mixture was concentrated. The residue was recrystallized from benzotrifluoride.

후처리

  1. additionwere added in portions
  2. temperaturein the course of which heating
  3. additionwere added
  4. extractionthe mixture was extracted 4 times at pH=10 with ethyl acetate
  5. dry with materialthe combined organic phases were dried with MgSO4
  6. concentrationthe mixture was concentrated
  7. customThe residue was recrystallized from benzotrifluoride

출처 및 근거

ORD 기록
ord-42bb7238e168470ba40fa53fcde8a962
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09339032B2

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