Sodium hydride → HCID 20071554, compound

HRID 981049Notes

Reaction equation

HRID 981049 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[CH3:14])[N:10]=[C:9]1[NH:15][C:16]3[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][C:21]=3[C:8]1=[N:7]2.Cl.[CH3:24][N:25]([CH2:27][CH2:28]Cl)[CH3:26]>CS(C)=O>[CH3:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[CH3:14])[N:10]=[C:9]1[N:15]([CH2:28][CH2:27][N:25]([CH3:26])[CH3:24])[C:16]3[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][C:21]=3[C:8]1=[N:7]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10853541HCID 10853541, compoundHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 20071554HCID 20071554, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
35 °C

Procedure

To a suspension of 5.38 g sodium hydride (0.22 mole) in 600 ml dry dimethylsulphoxide maintained at 35° C. 32.6 g 2,3-dimethyl-9-bromo-6H-indolo(2,3-b)quinoxaline (0.10 mol) is added under nitrogen and with good stirring. 30 minutes after completed addition 15.9 g N,N-dimethylamino-2-chloroethane-HCl (0.11 mole) are added at 35° C. The mixture is stirred at 35° C. for four hours and then the solvent is distilled off in vacuum at room temperature. The residue is dissolved after soaking out with water in methylacetate and slowly cooled to -30° C. whereby the base crystallizes out. Yield 22 g, 55%, mp. 146°-147° C.

Workup

  1. custom30 minutes
  2. additionare added at 35° C
  3. distillationthe solvent is distilled off in vacuum at room temperature
  4. dissolutionThe residue is dissolved
  5. temperatureslowly cooled to -30° C. whereby the base
  6. customcrystallizes out

Sources & evidence

ORD record
ord-b00cf8bd63de4b0f8616334dbe3dca71
Source dataset
uspto-grants-1991_02
Patent number
US04990510

Reaction notes

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