Sulfamic Acid → 2-[5-(2,4Dioxopent-3-ylazo)-2-propoxyphenyl]-8-azapurin-6-one

HRID 1863130Notes

Reaction equation

HRID 1863130 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][CH2:20][CH3:21])=[C:6]([C:8]2[N:16]=[C:15]3[C:11](=[N:12][N:13]=[N:14]3)[C:10](=[O:17])[N:9]=2)[CH:7]=1.Cl.[NH2:23]C1C=CC(OCCC)=C(C2N=C3C(=NN=N3)C(=O)N=2)C=1.N([O-])=O.[Na+].S(=O)(=O)(O)N.N(O)=O.[C:56]([CH2:59][C:60](=[O:62])[CH3:61])(=[O:58])[CH3:57].C([O-])(=O)C.[Na+]>Cl.O.C(O)C>[O:58]=[C:56]([CH:59]([N:23]=[N:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH2:19][CH2:20][CH3:21])=[C:6]([C:8]2[N:16]=[C:15]3[C:11](=[N:12][N:13]=[N:14]3)[C:10](=[O:17])[N:9]=2)[CH:7]=1)[C:60](=[O:62])[CH3:61])[CH3:57]

Participants

11

Reactant 7

HCID 5987Sulfamic AcidHCID 24529Nitrous AcidHCID 31261AcetylacetoneHCID 517045Sodium AcetateHCID 203929612-(5-Amino-2-propoxyphenyl)-8-azapurin-6-oneHCID 203929772-(5-Amino-2-propoxyphenyl)-8-azapurin-6-one hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 203929742-[5-(2,4Dioxopent-3-ylazo)-2-propoxyphenyl]-8-azapurin-6-one

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

2-(5-Amino-2-propoxyphenyl)-8-azapurin-6-one (1.5 g) was dissolved in a hot mixture of concentrated hydrochloric acid (4 ml) and water (20 ml). The solution was then cooled to 0° C. to give a suspension of 2-(5-amino-2-propoxyphenyl)-8-azapurin-6-one hydrochloride. The stirred suspension was treated with a solution of sodium nitrite (0.5 g) in water (2 ml) during 10 minutes. After stirring for one hour at 0° C., a sufficient quantity of sulphamic acid was added to decompose the excess of nitrous acid. The resulting ice-cold solution was then added, dropwise, to a stirred mixture of acetylacetone (2 ml), ethanol (20 ml), water (10 ml) and sodium acetate (5 g) at 0° C. during 30 minutes. After a further 30 minutes, the thick yellow mixture was filtered, and the precipitate was washed with water and sucked dry. Recrystallisation from a mixture of dimethylformamide and methanol gave 2-[5-(2,4dioxopent-3-ylazo)-2-propoxyphenyl]-8-azapurin-6-one (1.4 g), m.p. 288°-290° C. (with decomposition).

Workup

  1. customto give
  2. waitAfter a further 30 minutes
  3. filtrationthe thick yellow mixture was filtered
  4. washthe precipitate was washed with water
  5. customsucked dry
  6. customRecrystallisation
  7. additionfrom a mixture of dimethylformamide and methanol

Sources & evidence

ORD record
ord-3ccc3a7463084988b322d831dfb2283a
Source dataset
uspto-grants-1979_09
Patent number
US04167568

Reaction notes

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