Dimethylformamide → HCID 15587310, compound
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].CN(C)C=O.S(Cl)(Cl)=O.[NH:35]1[CH2:40][CH2:39][S:38][CH2:37][CH2:36]1>C(O)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]([N:35]4[CH2:40][CH2:39][S:38][CH2:37][CH2:36]4)(=[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
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)benzenesulfonic acid (10.0 g, 0.0274 moles) and N,N-dimethylformamide (300 ml) is cooled to 0° C. and treated with thionyl chloride (6.5 g, 0.055 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 thiomorpholine (14.2 g, 0.137 moles) in one portion. The resulting mixture is stirred one hour, poured into three liters of water, and filtered. The solids thus obtained are tritruated with ethanol and dried at 48° in a vacuum oven to yield 11.9 grams of 4-[[4-(1,3-diethyl-2,3,6,7-tetrahydro-2,6-dioxo-1H-purin-8-yl)phenyl]sulfonyl]thiomorpholine, mp 340°-350° C.(d).
Workup
- additionWhen the addition
- temperatureto warm to ambient temperature
- customresults
- stirringThe resulting mixture is stirred one hour
- filtrationfiltered
- customThe solids thus obtained
- customdried at 48° in a vacuum oven
Sources & evidence
- ORD record
- ord-038bf886de67419088dcbb807ca8f9f9
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04452788
Reaction notes
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