Thionyl Chloride → 4-(1,3-Diethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-N-(2-dimethylamino-ethyl)-benzenesulfonamide

HRID 1262521Notes

Reaction equation

HRID 1262521 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]([OH:22])(=[O:21])=O)=[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)=O.[CH3:30][N:31]([CH2:33][CH2:34][NH2:35])[CH3:32]>CN(C)C=O>[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][N:31]([CH3:32])[CH3:30])(=[O:21])=[O:22])=[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 24386Thionyl ChlorideHCID 66053N,N-DimethylethylenediamineHCID 155873004-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid

Product 1

HCID 155873044-(1,3-Diethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)-N-(2-dimethylamino-ethyl)-benzenesulfonamideYield 71.1%

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, (7.0 g, 0.019 moles) and N,N-dimethylformamide (125 ml) is cooled to 0°, and treated with thionyl chloride (4.6 g, 0.038 moles). When the addition is complete, the reaction mixture is permitted to warm to ambient temperature, and stirred vigorously for one hour. The resulting slurry is cooled to 0°, and treated with unsym dimethylethylenediamine (8.8 g, 0.10 mole) and allowed to warm to ambient temperature. The reaction mixture is concentrated on a rotary evaporator, the residue is taken up in cool water and filtered. The solid thus obtained is recrystallized from ethanol and dried at 78° in a drying pistol to give 5.87 grams of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)-N-[2-(dimethylamino)ethyl]benzene-sulfonamide, mp 264°-265° C.(d).

Workup

  1. temperatureis cooled to 0°
  2. additionWhen the addition
  3. temperatureThe resulting slurry is cooled to 0°
  4. temperatureto warm to ambient temperature
  5. concentrationThe reaction mixture is concentrated on a rotary evaporator
  6. filtrationfiltered
  7. customThe solid thus obtained
  8. customis recrystallized from ethanol
  9. customdried at 78° in a drying pistol

Sources & evidence

ORD record
ord-03014f1ffda242438042e7200bc6a16f
Source dataset
uspto-grants-1984_06
Patent number
US04452788

Reaction notes

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