Hydrochloric Acid → 3-[(4-Chromanylidene)amino]-2-oxazolidinone

HRID 2420001Notes

Reaction equation

HRID 2420001 reaction equation
[NH2:1][N:2]1[CH2:6][CH2:5][O:4][C:3]1=[O:7].O.Cl.[O:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=O)[CH2:12][CH2:11]1>C(O)C>[O:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13](=[N:1][N:2]2[CH2:6][CH2:5][O:4][C:3]2=[O:7])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 657253-Amino-2-oxazolidinoneHCID 68110Chromanone

Product 1

HCID 706151053-[(4-Chromanylidene)amino]-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 62 g (0.61 mole) portion of 3-amino-2-oxazolidinone was charged in a 500 ml, 3-necked flask equipped with a thermometer, stirrer and reflux condenser, and treated successively with 92 ml of H2O, 8 ml of 10% HCl and 42 g (0.28 mole) of 4-chromanone in 200 ml of ethanol. The reaction mixture was refluxed for 36 hrs., stripped in vacuo to one-half volume and cooled in the refrigerator overnight. The slurry was filtered and the white crystalline solid washed with 50 ml of isopropanol then 200 ml of ether and dried; m.p. 105°-108°. Yield: 44 g (68%).

Workup

  1. customequipped with a thermometer, stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was refluxed for 36 hrs
  4. temperaturecooled in the refrigerator overnight
  5. filtrationThe slurry was filtered
  6. washthe white crystalline solid washed with 50 ml of isopropanol
  7. dry with material200 ml of ether and dried

Sources & evidence

ORD record
ord-41981f197c8f4fa58047be370949744a
Source dataset
uspto-grants-1978_08
Patent number
US04108862

Reaction notes

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