Sodium hydride → HCID 21559921, compound

HRID 1578375Notes

Reaction equation

HRID 1578375 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:16]1[C:17]2[C:22]([N:23]=[C:24]3[C:29]=1[CH:28]=[CH:27][CH:26]=[CH:25]3)=[CH:21][CH:20]=[CH:19][CH:18]=2>CN(C=O)C>[CH:18]1[C:17]2[C:22](=[N:23][C:24]3[C:29]([C:16]=2[CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 710139-ChloroacridineHCID 104196Methyl 4-chlorophenylacetate

Product 1

HCID 21559921HCID 21559921, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

After a mixture of DMF (250 ml), methyl p-chlorophenylacetate (25.9 g, 140 mmol) and NaH (211 mmol) was stirred at room temperature for 1 hour, 9-chloroacridine (15.0 g, 70.2 mmol) dissolved in 250 ml of DMF was added slowly. The resultant reaction mixture was stirred at room temperature for 18 hours. This reaction mixture was then poured onto 1.5 l. of an ice/H2O mixture and extracted with CHCl3 (500 ml). The CHCl3 extract was washed with H2O (3×500 ml) and dried over MgSO4. Evaporation of the CHCl3 extract gave a crude residual solid which was recrystallized from cyclohexane; yield, 20.2 g (79.4%), mp 192°-193°.

Workup

  1. additionwas added slowly
  2. customThe resultant reaction mixture
  3. stirringwas stirred at room temperature for 18 hours
  4. additionThis reaction mixture was then poured onto 1.5 l
  5. extractionof an ice/H2O mixture and extracted with CHCl3 (500 ml)
  6. extractionThe CHCl3 extract
  7. washwas washed with H2O (3×500 ml)
  8. dry with materialdried over MgSO4
  9. customEvaporation of the CHCl3
  10. extractionextract
  11. customgave a crude residual solid which
  12. customwas recrystallized from cyclohexane
  13. customyield

Sources & evidence

ORD record
ord-220874d1691b40b99e4b3119fd204d7b
Source dataset
uspto-grants-1976_02
Patent number
US03936457

Reaction notes

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