Sodium hydride → HCID 18434021, compound

HRID 1384856Notes

Reaction equation

HRID 1384856 reaction equation
[H-].[Na+].[CH2:3]([NH:7][C:8](=[S:19])[NH:9][C:10]1[S:11][CH:12]=[CH:13][C:14]=1[C:15](OC)=[O:16])[CH2:4][CH2:5][CH3:6]>O1CCCC1>[CH2:3]([N:7]1[C:15](=[O:16])[C:14]2[CH:13]=[CH:12][S:11][C:10]=2[NH:9][C:8]1=[S:19])[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 53940306HCID 53940306, compound

Product 1

HCID 18434021HCID 18434021, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a sulfonation flask, 0.2 g (0.0049 mol) of a ca. 60% sodium hydride dispersion is added to 20 ml absolute tetrahydrofurane. Then 1.29 g (0.0047 mol) of methyl 2-(3-butylthioureido)thiophene-3-carboxylate, dissolved in 10 ml absolute tetrahydrofurane are added dropwise, such that the internal temperature remains constant at about 25° C. The mixture is stirred at reflux temperature for 3 hours and then the solvent is removed in a water-jet vacuum and the residue taken up in ethylacetate/water. After addition of acetic acid the mixture is extracted three times with ethylacetate and the organic phase dried over sodium sulfate. After removal of the solvent in a water-jet vacuum, 1.06 g of 3-butyl-2-thioxo-2,3-dihydro-1H-thieno[2.3-d]pyrimidin-4-one are obtained in the form of a brown powder having a melting point of 200-203° C.

Workup

  1. additionare added dropwise, such that the internal temperature
  2. customremains constant at about 25° C
  3. temperatureat reflux temperature for 3 hours
  4. customthe solvent is removed in a water-jet vacuum
  5. additionAfter addition of acetic acid the mixture
  6. extractionis extracted three times with ethylacetate
  7. dry with materialthe organic phase dried over sodium sulfate
  8. customAfter removal of the solvent in a water-jet vacuum, 1.06 g of 3-butyl-2-thioxo-2,3-dihydro-1H-thieno[2.3-d]pyrimidin-4-one
  9. customare obtained in the form of a brown powder

Sources & evidence

ORD record
ord-faa015f17a694e5084595cd29e859734
Source dataset
uspto-grants-2001_07
Patent number
US06262058B1

Reaction notes

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