Monobasic potassium phosphate → HCID 686817, compound

HRID 865666Notes

Reaction equation

HRID 865666 reaction equation
P([O-])(O)(O)=O.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2([NH:18]C(OCC(Cl)(Cl)Cl)=O)[CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:12][CH:13]=1>C1COCC1.[Zn]>[Cl:7][C:8]1[CH:9]=[C:10]([C:14]2([NH2:18])[CH2:17][CH2:16][CH2:15]2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 516951Monobasic potassium phosphateHCID 23374563HCID 23374563, compound

Product 1

HCID 686817HCID 686817, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

According to the procedure of Just and Grozinger (Just, G. and K. Grozinger, Synthesis 457 (1976)), a rapidly stirring mixture of 1.0 ml of 1M potassium dihydrogenphosphate and Zn powder (1.0 g) was treated dropwise during 1 minute with a solution of the product from Step 3 in 5 ml of THF. After 10 minutes, an exotherm to 28° C. was produced and the two-phase system gave way to a slurry. This mixture was stirred for 1 hour when it was filtered through celite; the filter cake was washed alternately with THF and H2O (twice each). The pooled filtrate was concentrated in vacuo and the aqueous residue was cooled and brought to pH 12-13 with 8% aqueous NaOH. This was extracted 3 times with CHCl3 ; the extracts were washed with H2O and then with brine. The pooled extract was dried (MgSO4) and concentrated to give 0.23 g (92%) of the titled product.

Workup

  1. customGrozinger, Synthesis 457 (1976)),
  2. customan exotherm to 28° C. was produced
  3. customthe two-phase system gave way to a slurry
  4. stirringThis mixture was stirred for 1 hour when it
  5. filtrationwas filtered through celite
  6. washthe filter cake was washed alternately with THF and H2O (twice each)
  7. concentrationThe pooled filtrate was concentrated in vacuo
  8. temperaturethe aqueous residue was cooled
  9. extractionThis was extracted 3 times with CHCl3
  10. washthe extracts were washed with H2O
  11. extractionThe pooled extract
  12. dry with materialwas dried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-364a82e583a34aac9bfc7ef05de679a8
Source dataset
uspto-grants-1996_10
Patent number
US05567722

Reaction notes

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