Sulfuric Acid → HCID 18381640, compound

HRID 2268840Notes

Reaction equation

HRID 2268840 reaction equation
CC1(C)C[O:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=2[C:15](=O)[CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:3]1.OS(O)(=O)=O.O.[NH2:34]N.[OH-].[Na+]>C(O)(=O)C.O.C(O)C>[CH3:14][O:13][C:10]1[CH:9]=[C:8]2[C:7](=[CH:12][CH:11]=1)[C:4](=[O:5])[NH:3][N:34]=[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 18381626HCID 18381626, compound

Product 1

HCID 18381640HCID 18381640, compoundYield 29.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of 1-[2-(4,4-dimethyl-4,5-dihydro-oxazol-2-yl)-5-methoxy-phenyl]-5-phenyl-pentan-1-one (0.37 g, 1 mmole), prepared as described in example 18, in 5 ml of a mixture of water (0.5 ml), ethanol (5 ml), concentrated H2SO4 (0.4 ml) up to 10 ml with ethanol, was stirred at reflux for 20 hours, then concentrated to small volume, taken up in water, extracted with ethyl ether and the ethereal phase was washed with water, anhydrified and brought to dryness. The resultant oil was dissolved in acetic acid (10 ml) and dropwise added, under N2, with a solution of hydrazine monohydrate (0.45 ml, 3 mmoles) in acetic acid (2 ml). The mixture was stirred for 3 hours at 80° C., then overnight at room temperature and at 80° C. for further 5 hours, cooled, almost brought to dryness, taken up in water, basified with NaOH, extracted more times with ethyl acetate. The organic phases were washed with water/NaCl, anhydrified and concentrated. The residue was flash chromatographed (eluent: petroleum/ethyl acetate 6:4) to give 0.09 g of the title compound (yield: 29%).

Workup

  1. temperatureat reflux for 20 hours
  2. concentrationconcentrated to small volume
  3. extractionextracted with ethyl ether
  4. washthe ethereal phase was washed with water
  5. dissolutionThe resultant oil was dissolved in acetic acid (10 ml)
  6. stirringThe mixture was stirred for 3 hours at 80° C.
  7. temperaturecooled
  8. extractionextracted more times with ethyl acetate
  9. washThe organic phases were washed with water/NaCl, anhydrified
  10. concentrationconcentrated
  11. customchromatographed (eluent: petroleum/ethyl acetate 6:4)

Sources & evidence

ORD record
ord-c8125ce9395d40b4ab9cb2d8d7b7362a
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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