Propylamine → HCID 22966909, compound

HRID 2305999Notes

Reaction equation

HRID 2305999 reaction equation
[CH2:1]([NH2:4])[CH2:2][CH3:3].[N:5]([C:8]1[S:9][CH:10]=[CH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14])=[C:6]=[S:7]>O1CCCC1>[CH2:1]([NH:4][C:6](=[S:7])[NH:5][C:8]1[S:9][CH:10]=[CH:11][C:12]=1[C:13]([O:15][CH3:16])=[O:14])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 7852PropylamineHCID 2759916Methyl 2-isothiocyanatothiophene-3-carboxylate

Product 1

HCID 22966909HCID 22966909, compoundYield 597.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a sulfonation flask, 13.5 g (0.023 mol) of n-propylamine are added dropwise to 350 ml of tetrahydrofurane and 41.3 g (0.021 mol) of methyl 2-isothiocyanatothiophene-3-carboxylate, such that the internal temperature does not arise above 40° C. The reaction mixture is then stirred for 4 hours at reflux temperature and then the tetrahydrofurane is 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 crude product, which is purified by column chromatography over silica gel (eluant: ethyl acetate/hexane=1:3). 32.4 g of methyl 2-(3-propylthioureido)thiophene-3-carboxylate are obtained in the form of a beige powder having a melting point of 123-126° C.

Workup

  1. customdoes not arise above 40° C
  2. temperatureat reflux temperature
  3. customthe tetrahydrofurane is 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
  7. customgiving the crude product, which
  8. customis purified by column chromatography over silica gel (eluant: ethyl acetate/hexane=1:3)

Sources & evidence

ORD record
ord-12837e1020a04587acea3c212a3d7b2b
Source dataset
uspto-grants-2002_08
Patent number
US06441169B1

Reaction notes

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