Adenine → HCID 21216970, compound

HRID 1586521Notes

Reaction equation

HRID 1586521 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[C:11](Cl)(=[O:14])[CH:12]=[CH2:13].Cl>C(=O)(O)[O-]>[C:11]([C:2]1[N:3]=[C:4]2[C:8]([NH:7][CH:6]=[N:5]2)=[C:9]([NH2:10])[N:1]=1)(=[O:14])[CH:12]=[CH2:13]

Participants

5

Reactant 3

HCID 190AdenineHCID 313Hydrochloric AcidHCID 13140Acryloyl chloride

Product 1

HCID 21216970HCID 21216970, compound

Reagents, catalysts & solvents 1

HCID 769Bicarbonate IonSolvent

Procedure

Adenine (0.27 g, 0.002 mole) was dissolved in 7 ml of bicarbonate buffer (pH 8), cooled to 0°-4° C., and acrylic acid chloride (1.1 g, 0.01 mole) was added with intense stirring for 1 hour. The solution was acidified with 1 M HCl until pH 6 was obtained, the solvent was evaporated in vacuum and the formed white precipitate was recrystallized from dimethyl sulfoxide. The yield of the AAD was 70%. The IR spectra displayed no absorption bands at 1650 cm-1 (bending vibrations of NH2 groups); however, absorption bands appeared at 1680 (amide-1), 1540 (amide-II), and 1290 (amide-III). These data confirm that a compound of AAD having the above formula was prepared.

Workup

  1. temperaturecooled to 0°-4° C.
  2. customwas obtained
  3. customthe solvent was evaporated in vacuum
  4. customthe formed white precipitate was recrystallized from dimethyl sulfoxide
  5. customno absorption bands at 1650 cm-1 (bending vibrations of NH2 groups)
  6. customhowever, absorption bands
  7. customwas prepared

Sources & evidence

ORD record
ord-028ad39085c0404a9336f4bc2d662827
Source dataset
uspto-grants-1999_08
Patent number
US05945457

Reaction notes

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