Dimethylformamide → N-dimethylaminomethyleneguanine

HRID 1756265Notes

Reaction equation

HRID 1756265 reaction equation
[NH:1]1[C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=[C:2]1[NH2:3].[CH3:12][N:13]([CH3:16])[CH:14]=O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>>[CH3:12][N:13]([CH:16]=[N:3][C:2]1[NH:1][C:10](=[O:11])[C:9]2[NH:8][CH:7]=[N:6][C:5]=2[N:4]=1)[CH3:14]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 135398634Guanine

Product 1

HCID 136087653N-dimethylaminomethyleneguanineYield 71%

Conditions

Temperature
30 °C

Procedure

15.1 g (0.1 mol) of guanine (manufactured by Sumika Fine Chemicals Co., Ltd.) was added to 175.4 g (2.4 mol) of N,N-dimethylformamide, and then 23.0 g (0.15 mol) of phosphorus oxychloride was added drop by drop, followed by stirring at 30° C. for 1 hour. The reaction mixture was added to 500 ml of ice water, and then neutralized with 75.6 g (0.9 mol) of sodium hydrogen carbonate. The precipitating crystal was collected by filtration and washed with 50 ml of water to yield 14.6 g (0.07 mol) of a white crystal of N-dimethylaminomethyleneguanine (yield 71%). Its properties are as follows:

Workup

  1. filtrationThe precipitating crystal was collected by filtration
  2. washwashed with 50 ml of water

Sources & evidence

ORD record
ord-028ec083468e44e7a664b544ecc8577a
Source dataset
uspto-grants-1995_08
Patent number
US05440037

Reaction notes

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