Ammonia → HCID 54530041, compound

HRID 439413Notes

Reaction equation

HRID 439413 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH-:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N.[C:18](=O)([O-])[O-:19].[K+].[K+].C=O>>[O:1]([C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([NH:13][CH2:18][OH:19])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 712Formaldehyde2×HCID 11430Potassium CarbonateHCID 178514230HCID 178514230, compound

Product 1

HCID 54530041HCID 54530041, compoundYield 267.2%

Procedure

A flask was charged with 3-phenoxybenzoylamide (2.07 g, 9.8 mmol)(prepared from the corresponding acid chloride and concentrated ammonia), potassium carbonate (1.3 mL, 4% aqueous solution, 3.8 mmol), and aqueous formaldehyde (1.1 mL, 37% aqueous solution, 13.6 mmol). The resulting suspension was heated to reflux to give a two-phased solution. Addition of more aqueous formaldehyde (3 mL, 37 mmol) gave a homogeneous solution which was heated at reflux for 4 h. The reaction solution was cooled and partitioned between brine and ethyl acetate. The aqueous layer was dram off and extracted with ethyl acetate (2×). The combined organic layers were washed (2×, brine), dried (Na2SO4), and concentrated under vacuum to provide 2.47 gms of a viscous oil which solidified after vacuum drying. Recrystallization from cold ethyl acetate:hexanes provided the title compound as a colorless solid (1.38 g, 58%), mp 112.5-113° C.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux
  3. customto give a two-phased solution
  4. customgave a homogeneous solution which
  5. temperaturewas heated
  6. temperatureat reflux for 4 h
  7. temperatureThe reaction solution was cooled
  8. custompartitioned between brine and ethyl acetate
  9. extractionextracted with ethyl acetate (2×)
  10. washThe combined organic layers were washed (2×, brine)
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-17d59a417848433a95c133089bc46b65
Source dataset
uspto-grants-1996_05
Patent number
US05514702

Reaction notes

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