Ethanol → HCID 19419819, compound

HRID 2210978Notes

Reaction equation

HRID 2210978 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([O:9][CH2:10][CH3:11])[N:3]=1.C(N(CC)CC)C.C(O)C.O.[NH2:23][NH2:24]>O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:23][NH2:24])[N:5]=[C:4]([O:9][CH2:10][CH3:11])[N:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)2×HCID 98370152-Ethoxy-4,6-dichloropyrimidine

Product 1

HCID 19419819HCID 19419819, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 50.0 g of 95 percent purity (0.246 mol) 4,6-dichloro-2-ethoxypyrimidine, 26.9 g (0.266 mol) of triethylamine, 200 mL of ethanol, and 200 g of water was prepared and cooled to 5° C. To this was added 13.4 g (0.266 mol) of hydrazine hydrate over a 15-min period with stirring and cooling at about 5° C. The mixture was stirred and allowed to warm to ambient temperature overnight. It became very thick, but approximately 10 percent of the starting material remained. Another 1.3 g (0.026 mol) of hydrazine hydrate was added and stirring was continued for another 4 hours. The solids that formed were recovered by vacuum filtration and were washed twice with 100 mL portions of water and then with 100 mL of acetonitrile. The title compound, which was obtained as a white powder melting at 170°-173° C., amounted to 43.9 g (88 percent of theory).

Workup

  1. customwas prepared
  2. temperaturecooling at about 5° C
  3. stirringThe mixture was stirred
  4. temperatureto warm to ambient temperature overnight
  5. stirringstirring
  6. customThe solids that formed
  7. filtrationwere recovered by vacuum filtration
  8. washwere washed twice with 100 mL portions of water

Sources & evidence

ORD record
ord-b2243c5daa214bdfb34aa5925decee1f
Source dataset
uspto-grants-1995_10
Patent number
US05461153

Reaction notes

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