Hydrochloric Acid → 4-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium

HRID 31722

반응식

HRID 31722 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+]([O-])=O)[C:5]([CH3:12])=[CH:4][N+:3]=1[O-:13].[ClH:14].C(=O)([O-])[O-].[K+].[K+]>C(OC(C)C)(C)C.CCCCCC.O.CN(C)C=O>[Cl:14][C:6]1[C:5]([CH3:12])=[CH:4][N+:3]([O-:13])=[C:2]([CH3:1])[C:7]=1[CH3:8]

참가 물질

8

반응물 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxide

생성물 1

HCID 27791414-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium수율 83.1%

시약·촉매·용매 4

HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 7914Diisopropyl Ether용매HCID 8058Hexane용매

반응 조건

온도
70 °C

실험 절차

To 2,3,5-trimethyl-4-nitropyridine1-oxide (850 g, 4.67 mol), water (400 g) and 36% concentrated hydrochloric acid (1.69 kg) was added and the mixture was heated to 70° C. To the mixture, N,N-dimethylformamide (115 mL) was added and then the resultant mixture was heated to 100° C. After completion of the reaction, the reaction mixture was cooled to 20° C. and poured into a mixture of potassium carbonate (1.40 kg) and water (7 L). The mixture was extracted with chloroform (1.0 L×3), the organic layer dried over sodium sulfate and concentrated. The obtained crude product was stirred for 2 hours in a mixture of diisopropyl ether (500 mL) and n-hexane (1.0 L), and thereafter, sucking filtration was performed. The obtained wet product was dried under vacuum overnight to obtain a desired product (666.4 g).

후처리

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to 20° C.
  3. extractionThe mixture was extracted with chloroform (1.0 L×3)
  4. dry with materialthe organic layer dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe obtained crude product
  7. filtrationfiltration
  8. customThe obtained wet product was dried under vacuum overnight

출처 및 근거

ORD 기록
ord-fc7aa3e18e564e2f9ac740f48e7e47e0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425634B2

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