Toluene → HCID 14151562, compound

HRID 1708839Notes

Reaction equation

HRID 1708839 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])O[C:4]([CH2:11][CH2:12][CH3:13])=[C:3]1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15].[CH2:23]([NH2:27])[CH2:24][CH2:25][CH3:26].C1(C)C=CC=CC=1.[OH-].[Na+]>CO.C(OC(=O)C)C.O>[CH2:23]([N:27]1[C:6]([CH2:8][CH2:9][CH3:10])=[CH:7][C:2](=[O:1])[C:3]([C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:15])=[C:4]1[CH2:11][CH2:12][CH3:13])[CH2:24][CH2:25][CH3:26]

Participants

8

Reactant 4

HCID 1140TolueneHCID 8007ButylamineHCID 14798Sodium HydroxideHCID 14128630HCID 14128630, compound

Product 1

HCID 14151562HCID 14151562, compoundYield 62.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1 g (3.34 mmol) of 4-oxo-N-phenyl-2,6-dipropyl-4H-pyran-3-carboxamide, 0.37 g (5.01 mmol) of butylamine and 5 ml of toluene, 1 ml of 1N sodium hydroxide solution in methanol was added and stirred overnight at room temperature. After adding about 10 ml of water and about 10 ml of ethylacetate to the mixture, they were well shaken in a separatory funnel. The organic layer was washed with saturated sodium chloride solution, dried in an usual manner, concentrated and crystallized from toluene and cyclohexane to afford 737 mg of the title compound having m.p. 133.5°-136.5° C.

Workup

  1. additionwas added
  2. stirringwere well shaken in a separatory funnel
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. customdried in an usual manner
  5. concentrationconcentrated
  6. customcrystallized from toluene and cyclohexane

Sources & evidence

ORD record
ord-7c7674c2adf44e9f90abdb37cdeaca24
Source dataset
uspto-grants-1990_08
Patent number
US04946497

Reaction notes

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