Sodium → HCID 10003444, compound

HRID 973585Notes

Reaction equation

HRID 973585 reaction equation
[Na].[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[N:19]=[C:18]([N:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH3:21])[C:17]2[C:12](=[C:13]([OH:28])[CH:14]=[CH:15][CH:16]=2)[N:11]=1>C(O)C>[CH3:21][N:20]([CH3:22])[CH2:18][CH2:17][CH2:16][O:28][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:12]=1[N:11]=[C:10]([NH:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:2])[N:19]=[C:18]2[N:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:21]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 10405977HCID 10405977, compound

Product 1

HCID 10003444HCID 10003444, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium metal (103 mg, 4.49 mM) was dissolved in absolute ethanol (20 ml) and the solution added to a suspension of 2-[(2-methylphenyl)amino]-4-(N-methylphenylamino)-8-hydroxyquinazoline (1.6 g, 4.49 mM) in ethanol (100 ml). The mixture was heated until a clear solution was produced and then the ethanol was evaporated off. Toluene (25 ml) was added and again the mixture was evaporated to dryness. The residue was dissolved in toluene (50 ml) and to this solution was added a solution of N,N-dimethylaminopropylchloride (546 mg, 4.49 mM) in toluene (75 ml). The resulting mixture was heated at reflux temperature overnight, cooled, washed with water (×2), dried and evaporated to dryness, to give a browny-yellow oil. This oil was crystallised from ether/pentane to give the title compound (0.9 g) as buff-coloured flakes, m.p. 77°-79°.

Workup

  1. temperatureThe mixture was heated until a clear solution
  2. customwas produced
  3. customthe ethanol was evaporated off
  4. additionToluene (25 ml) was added
  5. customagain the mixture was evaporated to dryness
  6. dissolutionThe residue was dissolved in toluene (50 ml) and to this solution
  7. additionwas added a solution of N,N-dimethylaminopropylchloride (546 mg, 4.49 mM) in toluene (75 ml)
  8. temperatureThe resulting mixture was heated
  9. temperatureat reflux temperature overnight
  10. temperaturecooled
  11. washwashed with water (×2)
  12. customdried
  13. customevaporated to dryness
  14. customto give a browny-yellow oil
  15. customThis oil was crystallised from ether/pentane

Sources & evidence

ORD record
ord-743e485b94a24974a296b8e52ccac3b7
Source dataset
uspto-grants-1991_11
Patent number
US05064833

Reaction notes

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