Acetic Acid → 8-(2-Methoxy-4-aminocarbonyl-phenyl)-1H,3H-purin-2,6-dione

HRID 3877Notes

Reaction equation

HRID 3877 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9](O)=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[NH:20][C:19]2[C:18](=[O:21])[NH:17][C:16](=[O:22])[NH:15][C:14]=2[N:13]=1.[NH3:23].O.C(O)(=O)C>S(Cl)(Cl)=O.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([NH2:23])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[NH:20][C:19]2[C:18](=[O:21])[NH:17][C:16](=[O:22])[NH:15][C:14]=2[N:13]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 962WaterHCID 13532361HCID 13532361, compound

Product 1

HCID 201532438-(2-Methoxy-4-aminocarbonyl-phenyl)-1H,3H-purin-2,6-dione

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6228DimethylformamideSolvent2×HCID 24386Thionyl ChlorideSolvent2×

Procedure

A quantity of 2.3 gm of 8-(2-methoxy-4-carboxy-phenyl)-1H,-3H-purin-2,6-dione are refluxed for one hour in 50 ml of thionyl chloride with the addition of 1 drop of dimethylformamide. The excess thionyl chloride is drawn off, and the residue is stirred for 16 hours at ambient temperature with a solution of ammonia in dimethylformamide. The dimethylformamide is drawn off, the remainder is mixed with water and acidified with glacial acetic acid, and the product precipitated is filtered off.

Workup

  1. customthe product precipitated
  2. filtrationis filtered off

Sources & evidence

ORD record
ord-6a823073ab7c4f51901f88aec89eb947
Source dataset
uspto-grants-1988_02
Patent number
US04722929

Reaction notes

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