2-Methylbenzenesulfonic acid → HCID 13604742, compound

HRID 985942Notes

Reaction equation

HRID 985942 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.C1(C)C(S(O)(=O)=O)=CC=CC=1.CO[CH:29]1[CH:33]([CH2:34][N:35]([CH3:37])[CH3:36])[CH2:32][CH:31](OC)O1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:36][N:35]([CH2:34][C:33]1[CH:32]=[CH:31][N:1]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][CH:3]=2)[CH:29]=1)[CH3:37]

Participants

7

Reactant 4

HCID 69252-Methylbenzenesulfonic acidHCID 161928Ici 109,081HCID 516892Sodium BicarbonateHCID 20158836HCID 20158836, compound

Product 1

HCID 13604742HCID 13604742, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×

Procedure

10 millimoles of 6-(4-aminophenyl)-4,5-dihydro-5-methylpyridazinone in toluene were refluxed with 13 millimoles of toluenesulfonic acid and 12 millimoles of 2,5-dimethoxy-3-dimethylaminomethyltetrahydrofuran with the addition of a little dimethylformamide, this procedure being carried out under a water separator. When the reaction was complete, which was determined by thin layer chromatography, the major part of the solvent was stripped off, the residue was taken up in dimethylformamide and the solution was poured into saturated NaHCO3 solution. The aqueous phase was extracted with CH2Cl2 and the organic extract was dried over Na2SO4 and evaporated down in a rotary evaporator. The crude product was purified by column chromatography (SiO2, CH2Cl2 /CH3OH). 6-[4-(3-Dimethylaminomethylpyrrol-1-yl)-phenyl]-4,5-dihydro-5-methylpyridazinone was obtained, this substance being identical to that synthesized in Example 3A.

Workup

  1. extractionThe aqueous phase was extracted with CH2Cl2
  2. extractionthe organic extract
  3. dry with materialwas dried over Na2SO4
  4. customevaporated down in a rotary evaporator
  5. customThe crude product was purified by column chromatography (SiO2, CH2Cl2 /CH3OH)

Sources & evidence

ORD record
ord-e4debd70f32e483bb82834321382dbe1
Source dataset
uspto-grants-1987_12
Patent number
US04710496

Reaction notes

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