Hydrochloric Acid → HCID 178464510, 화합물

HRID 2211001노트

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HRID 2211001 반응식
[CH2:1]([N:3]([CH2:19][CH3:20])[S:4]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH2:17])=[C:9]([OH:18])[CH:8]=1)(=[O:6])=[O:5])[CH3:2].Cl.[N:22]([O-])=O.[Na+].[CH2:26]([N:28]1[C:32](=[O:33])[CH2:31][C:30]([CH3:34])=[N:29]1)[CH3:27].C([O-])(=O)C.[Na+].[OH-].[Na+]>C(O)C.O>[CH2:19]([N:3]([CH2:1][CH3:2])[S:4]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([N:17]=[N:22][C:31]2[C:30]([CH3:34])=[N:29][N:28]([CH2:26][CH3:27])[C:32]=2[OH:33])=[C:9]([OH:18])[CH:8]=1)(=[O:6])=[O:5])[CH3:20]

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 668049ST001145HCID 9971689N,N-Diethyl-3-hydroxy-4-amino-1-naphthalenesulfonamideHCID 23668193Sodium Nitrite

생성물 1

HCID 178464510HCID 178464510, 화합물수율 75.4%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 962Water용매

실험 절차

N,N-Diethyl-3-hydroxy-4-amino-1-naphthalenesulfonamide (2.94 g) was dissolved in 10 ml of ethanol and 10 g of ice was added. The reaction mixture was cooled in an ice bath to keep the temperature below 5° C. Hydrochloric acid (3 ml, 37% ) was added, followed by dropwise addition of a solution of 0.83 g sodium nitrite in 2 ml water and stirring was continued for 30 minutes. In a separate flask, to a solution of 1.26 g 2,4-dihydro- 2-ethyl-5-methyl-3H-pyrazol-3-one in 10 ml ethanol was added 11 ml of 20% aqueous sodium acetate followed by 9 ml of 10% aqueous sodium hydroxide, while the temperature was maintained below 5° C. The diazonium salt (as a suspension) was then added portionwise to the stirred solution of 2-dihydro-2-ethyl-5-methyl-3H-pyrazol-3-one at 5° C. and the resulting mixture stirred for 30 min at room temperature. The product was extracted with 100 ml chloroform, the organic layer was washed with 5% formic acid and water, and dried over anhydrous sodium sulfate; and the solvent evaporated to give crude 3.25 g N,N-diethyl-3-hydroxy-4-(5-hydroxy-3-methyl-1-ethyl-1H-pyrazol-4-yl)azo-1-naphthalenesulfonamide. The product was subjected to column chromatography (toluene) to give pure 2.55 g N,N-diethyl-3-hydroxy-4-(5-hydroxy-3-methyl-1-ethyl-1H-pyrazol-4-yl)azo-1-naphthalenesulfon amide which was crystallized from methanol to give dark red prisms, m.p. 174° -175° C.

후처리

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customthe temperature below 5° C
  3. temperaturewas maintained below 5° C
  4. stirringthe resulting mixture stirred for 30 min at room temperature
  5. extractionThe product was extracted with 100 ml chloroform
  6. washthe organic layer was washed with 5% formic acid and water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customand the solvent evaporated

출처 및 근거

ORD 기록
ord-82e52af0eec34beaa6567dc653bf54da
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05461155

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