Propylamine → HCID 16767826, compound

HRID 1384848Notes

Reaction equation

HRID 1384848 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[N:5]([C:8]1[CH:12]=[CH:11][S:10][C:9]=1[C:13](OC)=[O:14])=[C:6]=[S:7]>O1CCCC1>[CH2:1]([N:4]1[C:13](=[O:14])[C:9]2[S:10][CH:11]=[CH:12][C:8]=2[NH:5][C:6]1=[S:7])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 2777461methyl 3-isothiocyanatothiophene-2-carboxylate

Product 1

HCID 16767826HCID 16767826, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a sulfonation flask, 1.7 g (0.028 mol) of n-propylamine are added dropwise to 30 ml of tetrahydrofuran and 5.2 g (0.026 mol) of methyl 3-isothiocyanatothiophene-2-carboxylate, dissolved in 30 ml of tetrahydrofuran, such that the internal temperature does not rise above 35° C. The reaction mixture is then stirred for 16 hours at reflux temperature and the tetrahydrofuran is then removed in a water-jet vacuum. The residue is taken up in ethyl acetate and extracted three times with water. The organic phase is then dried over sodium sulfate and the solvent is removed in the water-jet vacuum, giving the 3-propyl-2-thioxo-2,3-di-hydro-1 H-thieno[3.2-d]pyrimidin-4-one crude product which can be purified by digestion in tert-butylmethyl ether. The slightly brownish powder (5.3 g) has a melting point of >230° C.

Workup

  1. customdoes not rise above 35° C
  2. temperatureat reflux temperature
  3. customthe tetrahydrofuran is then removed in a water-jet vacuum
  4. extractionextracted three times with water
  5. dry with materialThe organic phase is then dried over sodium sulfate
  6. customthe solvent is removed in the water-jet vacuum

Sources & evidence

ORD record
ord-dbeac288e52d47c08d9216b41135de6e
Source dataset
uspto-grants-2001_07
Patent number
US06262058B1

Reaction notes

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