Sulfuric Acid → Chloro-5-[(methylsulfonimidoyl)methyl]pyridine

HRID 909366노트

반응식

HRID 909366 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH3:11])=[O:10])=[CH:4][N:3]=1.[N-:12]=[N+]=[N-].[Na+].S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([CH3:11])(=[NH:12])=[O:10])=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 592659452-Chloro-5-[(methylsulfinyl)methyl]pyridine

생성물 1

HCID 59265933Chloro-5-[(methylsulfonimidoyl)methyl]pyridine수율 34%

시약·촉매·용매 1

HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

To a stirred mixture of 2-chloro-5-[(methylsulfinyl)methyl]pyridine (B) (7.34 g, 39 mmol) and sodium azide (4.04 g, 62 mmol) in chloroform (80 mL) cooled to 0° C. was slowly added sulfuric acid at a rate such that the temperature did not rise above 8° C. After the addition was over, the ice-water bath was removed and the mixture was heated at 55° C. for 2.5 h. The solvent was decanted into a separation funnel and the residue was stirred and dissolved in water. After a few minutes, the aqueous mixture was made basic to pH 8 by slowly adding solid Na2CO3 and then saturated with solid NaCl. The extra salt was removed by filtration (a portion of the filtrate was sucked into trap and was not recovered) and the filtrate was extracted with CH2Cl2 three times. The combined organic layer was dried over Na2SO4, filtered, concentrated and the residue was triturated in CH2Cl2-ether (1:10, v/v) solvent. The white solid was filtered, washed with CH2Cl2-ether (1:10, v/v) and dried to give 2.70 g of -chloro-5-[(methylsulfon-imidoyl)methyl]pyridine (C) in 34% yield as a white solid (m.p. 134.5-136° C.). LC-MS (ELSD): mass calcd for C7H9ClN2OS [M+H]+ 203.67. Found: 203.22.

후처리

  1. customdid not rise above 8° C
  2. additionAfter the addition
  3. customwas removed
  4. temperaturethe mixture was heated at 55° C. for 2.5 h
  5. customThe solvent was decanted into a separation funnel
  6. dissolutiondissolved in water
  7. waitAfter a few minutes
  8. additionby slowly adding solid Na2CO3
  9. customThe extra salt was removed by filtration (a portion of the filtrate
  10. customwas sucked into trap
  11. customwas not recovered) and the filtrate
  12. extractionwas extracted with CH2Cl2 three times
  13. dry with materialThe combined organic layer was dried over Na2SO4
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customthe residue was triturated in CH2Cl2-ether (1:10
  17. filtrationThe white solid was filtered
  18. washwashed with CH2Cl2-ether (1:10
  19. customv/v) and dried

출처 및 근거

ORD 기록
ord-388192b17ffc42419f811a13e90f90d0
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017788B2

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