N,N-Dimethyl-1,3-propanediamine → 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)-N-[3-(dimethylamino)-propyl]benzenesulfonamide monohydrochloride

HRID 1262522Notes

Reaction equation

HRID 1262522 reaction equation
[CH2:1]([N:3]1[C:11](=[O:12])[C:10]2[NH:9][C:8]([C:13]3[CH:18]=[CH:17][C:16]([S:19](O)(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[N:7][C:6]=2[N:5]([CH2:23][CH3:24])[C:4]1=[O:25])[CH3:2].S(Cl)([Cl:28])=O.[CH3:30][N:31]([CH3:36])[CH2:32][CH2:33][CH2:34][NH2:35]>CN(C)C=O>[ClH:28].[CH2:1]([N:3]1[C:11](=[O:12])[C:10]2[NH:9][C:8]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([NH:35][CH2:34][CH2:33][CH2:32][N:31]([CH3:36])[CH3:30])(=[O:21])=[O:20])=[CH:17][CH:18]=3)=[N:7][C:6]=2[N:5]([CH2:23][CH3:24])[C:4]1=[O:25])[CH3:2]

Participants

5

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 24386Thionyl ChlorideHCID 155873004-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid

Product 1

HCID 155873064-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)-N-[3-(dimethylamino)-propyl]benzenesulfonamide monohydrochlorideYield 22.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6,-dioxo-1H-purin-8-yl)benzenesulfonic acid, (5.0 g, 0.014 moles) and N,N-dimethylformamide (150 ml) is cooled to 0° and treated with thionyl chloride (3.3 g, 0.027 moles). When the addition is complete, the reaction mixture is permitted to warm to ambient temperature and stirred vigorously until a thick slurry is formed. To this slurry is added 3-(dimethylamino)propylamine (14 g, 0.137 moles) in one portion, the mixture is stirred until a clear solution is obtained, and concentrated on a rotary evaporator. The residue is taken up in water, filtered, recrystallized from ethanol, and dried at 78° to yield 1.53 grams of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)-N-[3-(dimethylamino)-propyl]benzenesulfonamide monohydrochloride, mp 291°-292° C.(d).

Workup

  1. temperatureis cooled to 0°
  2. additionWhen the addition
  3. customis formed
  4. stirringthe mixture is stirred until a clear solution
  5. customis obtained
  6. concentrationconcentrated on a rotary evaporator
  7. filtrationfiltered
  8. customrecrystallized from ethanol
  9. customdried at 78°

Sources & evidence

ORD record
ord-228bc59ecf1f4297a2a2eb2f373299ac
Source dataset
uspto-grants-1984_06
Patent number
US04452788

Reaction notes

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