Sodium hydride → HCID 53883952, compound

HRID 2049899Notes

Reaction equation

HRID 2049899 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][C:7]=3[O:8][C:4]=2[CH:3]=1.[H-].[Na+].[H][H].Cl[CH:21]([CH3:25])[C:22]([NH2:24])=[O:23]>O1CCCC1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[C:6]3[CH:12]=[C:11]([O:13][CH:21]([CH3:25])[C:22]([NH2:24])=[O:23])[CH:10]=[CH:9][C:7]=3[O:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 943852-ChloropropanamideHCID 119541287-Chloro-2-dibenzofuranolHCID 178418361HCID 178418361, compound

Product 1

HCID 53883952HCID 53883952, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

21.7 g (0.1 mole) 7-chloro-2-hydroxydibenzofuran is dissolved in 200 ml of tetrahydrofuran. To this solution is added 5.2 g sodium hydride (50% dispersion in oil) which was prewashed in petroleum ether. After hydrogen evolution had ceased, the solution was brought to reflux and 11.2 g (0.1 mole) of 2-chloropropionamide was added. The mixture was allowed to reflux for 8 hours. The solvent was evaporated and the crude product was washed with dilute acid and crystallized from methanol to yield 14.5 g, m.p. 185°-187° C. This Example corresponds to Example 20 in Table I.

Workup

  1. temperatureto reflux
  2. temperatureto reflux for 8 hours
  3. customThe solvent was evaporated
  4. washthe crude product was washed
  5. additionwith dilute acid
  6. customcrystallized from methanol
  7. customto yield 14.5 g, m.p. 185°-187° C

Sources & evidence

ORD record
ord-09e768c6007344ffa3928d87de5a43dd
Source dataset
uspto-grants-1980_04
Patent number
US04199346

Reaction notes

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