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Sulfurous Acid → HCID 19083162, 화합물

HRID 963669
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HRID 963669 반응식
C[N:2]1C=C2C(C=CC=C2)=N1.C([Li])CCC.S(=O)(O)O.NOS(O)(=O)=O.[OH-].[Na+].[CH3:28][N:29]1[C:37]([S:38]([O-:40])=[O:39])=[C:36]2[C:31]([CH:32]=[CH:33][CH:34]=[CH:35]2)=[N:30]1.[Li+]>C(OCC)C.O.CCCCCC>[CH3:28][N:29]1[C:37]([S:38]([NH2:2])(=[O:40])=[O:39])=[C:36]2[C:31]([CH:32]=[CH:33][CH:34]=[CH:35]2)=[N:30]1
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참가 물질

10

반응물 6

HCID 1100Sulfurous AcidHCID 14798Sodium HydroxideHCID 76284hydroxylamine-O-sulfonic acidHCID 1383642-Methyl-2H-indazoleHCID 23675697HCID 23675697, 화합물HCID 178418339Butyllithium

생성물 1

HCID 19083162HCID 19083162, 화합물
수율 58%

시약·촉매·용매 3

HCID 962Water용매2회HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

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온도
-30 °C

실험 절차

A solution containing 9.5 g (72 mmol) of 2-methyl-2H-indazole in 200 ml of ethyl ether, was cooled to -30° C., and 61.4 g (144 mmol) of n-butyl lithium (a 15% hexane solution) was dropwise added thereto. The mixture was stirred for one hour at the same temperature, and then an excess amount of sulfurous acid gas was blown thereinto for 3 hours at a temperature of not higher than -20° C. After completion of the reaction, the mixture was returned to room temperature, stirred for 12 hours and then diluted with ethyl ether. The product was subjected to filtration. The crystals were dried to obtain crude lithium 2-methyl-2H-indazole-3-sulfinate. This product was used for the subsequent reaction without purification. 48.8 g (430 mmol) of hydroxylamine-O-sulfonic acid was gradually added to a solution containing 17.2 g (430 mmol) of sodium hydroxide in water (300 ml) under cooling with ice (not higher than 10° C.). This solution was added all at once to a solution containing the crude lithium 2-methyl-2H-indazole-3-sulfinate previously prepared in water (100 ml), and then the mixture was stirred for 12 hours at room temperature. Formed crystals were collected by filtration to obtain 8.8 g (yield: 58%) of 2-methyl-2H-indazole-3-sulfonamide (slightly yellow granular crystals). Melting point: 181°-183° C.

후처리

  1. waitfor 3 hours at a temperature of not higher than -20° C
  2. customAfter completion of the reaction
  3. customwas returned to room temperature
  4. stirringstirred for 12 hours
  5. filtrationThe product was subjected to filtration
  6. customThe crystals were dried
  7. customto obtain crude lithium 2-methyl-2H-indazole-3-sulfinate
  8. customThis product was used for the subsequent reaction without purification
  9. temperatureunder cooling with ice (not higher than 10° C.)
  10. additionThis solution was added all at once to a solution
  11. stirringthe mixture was stirred for 12 hours at room temperature
  12. customFormed crystals
  13. filtrationwere collected by filtration

출처 및 근거

ORD 기록
ord-0e67187764064899b4c0a27d3da88450
출처 데이터셋
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05763616

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