Hydrochloric Acid → HCID 9820749, compound

HRID 1860244Notes

Reaction equation

HRID 1860244 reaction equation
[CH3:1][C:2]1[CH2:6][CH2:5][C:4]([P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])([CH3:7])[N:3]=1.[P:16]([O-:23])([O:20][CH2:21][CH3:22])[O:17][CH2:18][CH3:19].Cl.C([O-])(O)=O.[Na+].[Na+].[Cl-].C([O-])([O-])=O.[Na+].[Na+]>C(OCC)C>[CH2:10]([O:9][P:8]([C:4]1([CH3:7])[CH2:5][CH2:6][C:2]([P:16]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:23])([CH3:1])[NH:3]1)([O:12][CH2:13][CH3:14])=[O:15])[CH3:11]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 3780918DiethylphosphiteHCID 15497440HCID 15497440, compound

Product 1

HCID 9820749HCID 9820749, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Diethyl 2,5-dimethyl-1-pyrrolin-5-yl)phosphonate prepared in step 1 above (4.87 g; 0.0208 mol) is placed in a 250 ml two-necked round-bottomed flask and diethyl phosphite (5.89 g; 0.043 mol) is added dropwise thereto. The reaction is stirred at room temperature for 5 days. The reaction mixture is treated with 0.1 M HCl solution to pH=1 and is then extracted with diethyl ether. The aqueous phase obtained is: treated by addition of NaHCO3 to pH=10. The amine is salted out by adding NaCl and a large excess of Na2CO3 with stirring, in the presence of diethyl ether. The aqueous phase is then extracted with diethyl ether, after which the organic phase is dried over anhydrous Na2SO4. After filtration and evaporation under vacuum, the title compound is obtained in the form of an orange oil (3.41 g, 44%).

Workup

  1. extractionis then extracted with diethyl ether
  2. customThe aqueous phase obtained
  3. extractionThe aqueous phase is then extracted with diethyl ether
  4. dry with materialafter which the organic phase is dried over anhydrous Na2SO4
  5. filtrationAfter filtration and evaporation under vacuum

Sources & evidence

ORD record
ord-9a25ca8129e5425dbcae32fe94cbec0e
Source dataset
uspto-grants-2003_03
Patent number
US06528656B1

Reaction notes

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