Hydrochloric Acid → HCID 20326570, compound

HRID 2071361Notes

Reaction equation

HRID 2071361 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10](=NNC(N)=O)[CH2:11][P:12](=[O:17])([O:15][CH3:16])[O:13][CH3:14])=[N:6][CH:7]=1.Cl.[OH-:24].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10](=[O:24])[CH2:11][P:12](=[O:17])([O:15][CH3:16])[O:13][CH3:14])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53801769HCID 53801769, compound

Product 1

HCID 20326570HCID 20326570, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of dimethyl 3-(5-chloropyrid-2-yloxy)-2-semicarbazonopropylphosphonate (400 mg.), toluene (5 ml.) and 6N hydrochloric acid (1.0 ml.) was stirred at room temperature for 4.5 hours, and the pH of the reaction mixture was adjusted to about 4 by the dropwise addition of 5N sodium hydroxide solution. The organic layer was separated and the aqueous layer was washed with ethyl acetate (6 ml). The combined organic extracts were washed with a 1:1 v/v mixture of saturated brine and water (4 ml. then 2 ml.) and dried, and the solvents were evaporated under reduced pressure to give dimethyl 3-(5-chloropyrid-2-yloxy)-2-oxopropylphosphonate, RF = 0.43 (5% v/v methanol in ethyl acetate). The n.m.r. spectrum in deuteriochloroform showed the following characteristic peaks (δ values):

Workup

  1. customThe organic layer was separated
  2. washthe aqueous layer was washed with ethyl acetate (6 ml)
  3. washThe combined organic extracts were washed with a 1:1 v/v mixture of saturated brine and water (4 ml
  4. custom) and dried
  5. customthe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-6512d8786c544e07abf42aaaf25b118d
Source dataset
uspto-grants-1977_09
Patent number
US04046841

Reaction notes

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