1,2-Dichloroethane → N-dimethylaminomethyleneguanine

HRID 274998Notes

Reaction equation

HRID 274998 reaction equation
[CH3:1][N:2]([CH3:5])[CH:3]=O.S(Cl)(Cl)=O.ClCCCl.[NH:14]1[C:23](=[O:24])[C:22]2[NH:21][CH:20]=[N:19][C:18]=2[N:17]=[C:15]1[NH2:16]>O>[CH3:1][N:2]([CH:5]=[N:16][C:15]1[NH:14][C:23](=[O:24])[C:22]2[NH:21][CH:20]=[N:19][C:18]=2[N:17]=1)[CH3:3]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 135398634Guanine

Product 1

HCID 136087653N-dimethylaminomethyleneguanineYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

131.6 g (1.8 mol) of N,N-dimethylformamide and 42.8 g (0.36 mol) of thionyl chloride were added to 500 ml of 1,2-dichloroethane, and then 45.3 g (0.3 mol) of guanine (manufactured by Sumika Fine Chemicals Co., Ltd.) was added, followed by stirring at 80° C. for 6 hours. After cooling, the reaction mixture was added to 1000 ml of water to separate out the water layer, and then the water layer was neutralized with sodium hydrogen carbonate. The precipitating crystal was collected by filtration and washed with 100 ml of water to yield 52.6 g (0.255 mol) of a white crystal of N-dimethylaminomethyleneguanine (yield 85%).

Workup

  1. temperatureAfter cooling
  2. customto separate out the water layer
  3. filtrationThe precipitating crystal was collected by filtration
  4. washwashed with 100 ml of water

Sources & evidence

ORD record
ord-cbd837ab981b433dbf02f01d16d5a464
Source dataset
uspto-grants-1995_02
Patent number
US05391733

Reaction notes

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