Ethanol → HCID 21517759, compound

HRID 1283474Notes

Reaction equation

HRID 1283474 reaction equation
Cl[C:2]1[N:7]=[C:6](SC)[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][S:13](=[O:16])[CH2:12][CH2:11]2)[C:3]=1[N+:17]([O-:19])=[O:18].[CH3:20][CH2:21][O-:22].[Na+].[Na].[CH2:25]([OH:27])[CH3:26]>O>[CH2:21]([O:22][C:6]1[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][S:13](=[O:16])[CH2:12][CH2:11]2)[C:3]([N+:17]([O-:19])=[O:18])=[C:2]([O:27][CH2:25][CH3:26])[N:7]=1)[CH3:20]

Participants

6

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 53871742HCID 53871742, compound

Product 1

HCID 21517759HCID 21517759, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.0 gm (9.3 millimols) of 6-chloro-2-methylthio-5-nitro-4-(1-oxido-thiomorpholino)-pyrimidine (m.p. 128°-131°C) were added at room temperature to a sodium ethylate solution prepared from 0.22 gm (9.4 millimols) of sodium and 30 ml of ethanol, and the mixture was refluxed for 2 hours. After standing for 20 hours at room temperature, the reaction mixture was poured into water, the aqueous mixture was extracted several times with chloroform/ethanol, the combined extract solutions were evaporated to dryness, and the residue was recrystallized from ethyl acetate/petroleum ether. Yield: 2 gm (65% of theory); m.p. 130°-132°C.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. extractionthe aqueous mixture was extracted several times with chloroform/ethanol
  3. extractionthe combined extract solutions
  4. customwere evaporated to dryness
  5. customthe residue was recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-e066e3f0594349459520d73ff5c210dc
Source dataset
uspto-grants-1976_08
Patent number
US03975384

Reaction notes

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