Sodium Carbonate → HCID 86742627, compound

HRID 1086889Notes

Reaction equation

HRID 1086889 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:8][C:9](=[O:22])[N:10]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[CH3:7].O.O.O.[C:26]([O-:29])(=[O:28])[CH3:27].[Na+].[C:31](=O)([O-])[O-:32].[Na+].[Na+]>ClC(Cl)C.O.CN(C)C=O>[C:9]([OH:8])(=[O:22])/[CH:31]=[CH:27]\[C:26]([OH:29])=[O:28].[CH2:6]([O:8][C:9](=[O:22])[N:10]([N:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:31]=[O:32])[C:16]1[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=1)[CH3:7]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 14232111HCID 14232111, compoundHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 86742627HCID 86742627, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To cold dimethylformamide (9 g) was slowly added phosphorous oxychloride (18 g). After the reagent complex was formed, a solution of N-(4-pyridinyl)-N-(1H-pyrrol-1-yl)-carbamic acid ethyl ester (11 g) in 100 ml of dichloroethane was added. After stirring eight hours at 90°, the reaction mixture was cooled, hydrolyzed with a solution of sodium acetate trihydrate (20 g) in 100 ml of water, basified with sodium carbonate and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated to 14 g of an oil. This oil was purified by HPLC (silica, 20% ethyl acetate in dihcloromethane) to give 4 g of pure product which was converted to the maleate salt and recrystallized twice from isopropanol to give 3.4 g of needles, d 139°-140°.

Workup

  1. customAfter the reagent complex was formed
  2. temperaturethe reaction mixture was cooled
  3. extractionextracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with water and saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated to 14 g of an oil
  9. customThis oil was purified by HPLC (silica, 20% ethyl acetate in dihcloromethane)

Sources & evidence

ORD record
ord-ed1476f983f3419ea75cbb112bd6b9a1
Source dataset
uspto-grants-1991_07
Patent number
US05032599

Reaction notes

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