Ethanol → HCID 21517789, compound

HRID 1283453Notes

Reaction equation

HRID 1283453 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[C:4]([N:12]2[CH2:17][CH2:16][S:15][CH2:14][CH2:13]2)[N:3]=1.[CH3:18][CH2:19][O-:20].[Na+].[Na].C(O)C>CC(C)=O.O1CCOCC1>[CH2:19]([O:20][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][S:15][CH2:14][CH2:13]2)[N:5]=[C:6]([Cl:11])[C:7]=1[N+:8]([O-:10])=[O:9])[CH3:18]

Participants

7

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21517677HCID 21517677, compound

Product 1

HCID 21517789HCID 21517789, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
-20 °C

Procedure

14.8 gm (0.05 mol) of 4,6-dichloro-5-nitro-2-thiomorpholino-pyrimidine were dissolved in a mixture of 200 ml each of acetone and dioxane, and the solution was cooled to -20°C. A solution of sodium ethylate, prepared from 1.15 gm (0.05 mol) of sodium and 100 ml of ethanol, was added dropwise while stirring, at -20°C. The mixture was stirred another hour at room temperature, then poured over ice, and the product obtained thereby was recrystallized from isopropanol. Yield: 10.3 gm (67.5% of theory); m.p. 149°-150°C.

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred another hour at room temperature
  3. additionpoured over ice
  4. customthe product obtained
  5. customthereby was recrystallized from isopropanol

Sources & evidence

ORD record
ord-84dd98b808b34fda812f1bb048eab049
Source dataset
uspto-grants-1976_08
Patent number
US03975384

Reaction notes

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