Thionyl Chloride → HCID 15587303, compound

HRID 1262520Notes

Reaction equation

HRID 1262520 reaction equation
[K+].[CH2:2]([N:4]1[C:12](=[O:13])[C:11]2[NH:10][C:9]([C:14]3[CH:15]=[C:16]([S:20]([O-:23])(=[O:22])=O)[CH:17]=[CH:18][CH:19]=3)=[N:8][C:7]=2[N:6]([CH2:24][CH3:25])[C:5]1=[O:26])[CH3:3].S(Cl)(Cl)=O.[CH3:31][N:32]([CH2:34][CH2:35][NH2:36])[CH3:33]>CN(C=O)C>[CH2:2]([N:4]1[C:12](=[O:13])[C:11]2[NH:10][C:9]([C:14]3[CH:15]=[C:16]([S:20]([NH:36][CH2:35][CH2:34][N:32]([CH3:33])[CH3:31])(=[O:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)=[N:8][C:7]=2[N:6]([CH2:24][CH3:25])[C:5]1=[O:26])[CH3:3]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 66053N,N-DimethylethylenediamineHCID 23707919HCID 23707919, compound

Product 1

HCID 15587303HCID 15587303, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid monopotassium salt (4.6 g, 0.01 moles) and DMF (250 ml) is prepared and cooled to 0° C. To this solution is added thionyl chloride (7.14 g, 0.06 mole) and the mixture allowed to come to ambient temperature with vigorous stirring. To this slurry is added unsym dimethylethylenediamine (17.6 g, 0.2 moles). The resulting solution is concentrated on a rotary evaporator, the residue taken up in water, filtered, recrystallized twice from ethanol and dried at 48° to yield 0.78 grams of 3-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)-N-[2-(dimethylamino)ethyl]benzenesulfonamide, mp, 250°-251° C.

Workup

  1. customis prepared
  2. customto come to ambient temperature with vigorous stirring
  3. concentrationThe resulting solution is concentrated on a rotary evaporator
  4. filtrationfiltered
  5. customrecrystallized twice from ethanol
  6. customdried at 48°

Sources & evidence

ORD record
ord-7f71f9e4fdba4bb4b933b1a39aca1edc
Source dataset
uspto-grants-1984_06
Patent number
US04452788

Reaction notes

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