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Ammonia → 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonamide

HRID 1262525
Notes
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Reaction equation

HRID 1262525 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)=O.[NH3:30]>CN(C)C=O>[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]([NH2:30])(=[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24386Thionyl ChlorideHCID 155873004-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid

Product 1

HCID 155873094-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6dioxo-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 results. To this slurry is added N,N-dimethylformamide saturated with ammonia (100 ml). The resulting mixture is then saturated with gaseous ammonia and concentrated on a rotary evaporator. The residue is taken up in water, filtered, triturated with ethanol and dried at 68° C. to yield 2.9 grams of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonamide, mp 350°-353° C.(d).

Workup

  1. temperatureis cooled to 0°
  2. additionWhen the addition
  3. customresults
  4. concentrationsaturated with gaseous ammonia and concentrated on a rotary evaporator
  5. filtrationfiltered
  6. customtriturated with ethanol
  7. customdried at 68° C.

Sources & evidence

ORD record
ord-a8e089af6b88415ab001e9dc146292d2
Source dataset
uspto-grants-1984_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04452788

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes