Diisopropylamine → HCID 19594798, compound

HRID 612593Notes

Reaction equation

HRID 612593 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.C(N(CC)[C:16]([C:18]1[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[O:32][CH:33]([CH3:35])[CH3:34])=[CH:20][CH:21]=[C:22]([O:24][CH3:25])[CH:23]=1)=[O:17])C.[Cl-].[NH4+]>O1CCCC1>[CH:33]([O:32][C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:26]=1[C:19]1[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:18]=1[C:16]2=[O:17])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 19594892HCID 19594892, compoundHCID 178418339Butyllithium

Product 1

HCID 19594798HCID 19594798, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

Combine n-butyl lithium (22.00 mL of 2.5 M, 0.055 mole) and diisopropylamine (6.07 g, 0.060 mole), while stirring, in 150 mL tetrahydrofuran (THF) at -50° C. Wait approximately 5 minutes, then dropwise add N,N-diethyl-2'-isopropoxy-4-methoxy-biphenyl-2-carboxamide (3.80 g, 0.011 mole) dissolved in 50 mL THF. Remove the cooling source and allow the reaction to obtain ambient temperature, then stir while heating at 65° C. for 5 hours. The reaction changes color to orange, then to dark brown. Continue stirring the reaction overnight at ambient temperature overnight, then cool in an ice bath and neutralize with about 100 mL of a saturated solution of ammonium chloride. The reaction changes color to orange. Wash the THF solvent separately with brine (saturated sodium chloride) and dry over magnesium sulfate. Filter and concentrate to give a red liquid. Chromatography purification of this; material (20% ethyl acetate: 80% hexane) results in an orange liquid which solidifies when dried under high vacuum to give an orange solid (1.60 g, 50%). m.p. 89°-90° C.

Workup

  1. customRemove the cooling source
  2. customthe reaction
  3. customto obtain ambient temperature
  4. stirringContinue stirring
  5. customthe reaction overnight at ambient temperature overnight
  6. temperaturecool in an ice bath
  7. washWash the THF solvent separately with brine (saturated sodium chloride)
  8. dry with materialdry over magnesium sulfate
  9. filtrationFilter
  10. concentrationconcentrate
  11. customto give a red liquid
  12. customChromatography purification of this
  13. custommaterial (20% ethyl acetate: 80% hexane) results in an orange liquid which
  14. customdried under high vacuum

Sources & evidence

ORD record
ord-287ed278f078474683f88ec2770697af
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

Loading…