Sulfuric Acid → HCID 20392968, compound

HRID 1863131Notes

Reaction equation

HRID 1863131 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:19][CH2:20][CH2:21][CH3:22])=[C:7]([C:9]2[N:17]=[C:16]3[C:12](=[N:13][N:14]=[N:15]3)[C:11](=[O:18])[N:10]=2)[CH:8]=1)#[N:2].S(=O)(=O)(O)[OH:24]>O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:19][CH2:20][CH2:21][CH3:22])=[C:7]([C:9]2[N:17]=[C:16]3[C:12](=[N:13][N:14]=[N:15]3)[C:11](=[O:18])[N:10]=2)[CH:8]=1)(=[O:24])[NH2:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 20392959HCID 20392959, compound

Product 1

HCID 20392968HCID 20392968, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(5-Cyano-2-propoxyphenyl)-8-azapurin-6-one (2.0 g; prepared as described in Example 6) was carefully added with stirring to concentrated sulphuric acid (20 ml) during 10 minutes. The resulting solution was allowed to stand at room temperature for 3 hours, and then it was poured into iced water (100 ml) and the mixture was allowed to stand for 2 hours. The resulting solid was then filtered off and dissolved in aqueous sodium carbonate solution (2 N; 50 ml). This solution was treated with charcoal, filtered, and acidified by the addition of concentrated hydrochloric acid, and the resulting white solid was recrystallised from dimethylformamide. The recrystallised solid was dissolved in aqueous sodium carbonate solution (2 N; 50 ml) and the solution was acidified by the addition of concentrated hydrochloric acid and the resulting solid was filtered off to give 2-(5-carbamoyl-2-propoxyphenyl)-8-azapurin-6-one (0.9 g), m.p. 273°-275° C. (with decomposition).

Workup

  1. waitto stand for 2 hours
  2. filtrationThe resulting solid was then filtered off
  3. dissolutiondissolved in aqueous sodium carbonate solution (2 N; 50 ml)
  4. additionThis solution was treated with charcoal
  5. filtrationfiltered
  6. additionacidified by the addition of concentrated hydrochloric acid
  7. customthe resulting white solid was recrystallised from dimethylformamide
  8. dissolutionThe recrystallised solid was dissolved in aqueous sodium carbonate solution (2 N; 50 ml)
  9. additionthe solution was acidified by the addition of concentrated hydrochloric acid
  10. filtrationthe resulting solid was filtered off

Sources & evidence

ORD record
ord-c8c353178c6849a8989fad02cc9b96ae
Source dataset
uspto-grants-1979_09
Patent number
US04167568

Reaction notes

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